LoginSignup
13

More than 5 years have passed since last update.

Homebrewとopensslのインストール

Posted at

ESP32の開発環境ESP-IDFの導入中に

どうやらopensslのバージョンが古いようでインストールがerrorで終了しました。
opensslを新しくする必要があるようです。

MacBook-Pro:tools mgr206$ sudo easy_install pip
Password:
Searching for pip
Reading https://pypi.python.org/simple/pip/
Download error on https://pypi.python.org/simple/pip/: [SSL: TLSV1_ALERT_PROTOCOL_VERSION] tlsv1 alert protocol version (_ssl.c:590) -- Some packages may not be found!
Couldn't find index page for 'pip' (maybe misspelled?)
Scanning index of all packages (this may take a while)
Reading https://pypi.python.org/simple/
Download error on https://pypi.python.org/simple/: [SSL: TLSV1_ALERT_PROTOCOL_VERSION] tlsv1 alert protocol version (_ssl.c:590) -- Some packages may not be found!
No local packages or download links found for pip
error: Could not find suitable distribution for Requirement.parse('pip')

MacBook Proは開発用にあまり、というか全然使っていないので各種パッケージが古いのです。
opensslのバージョンを確認して見ると...2年以上前のリリースですね。更新していきましょう。

MacBook-Pro:tools mgr206$ openssl version
OpenSSL 0.9.8zh 14 Jan 2016

Homebrew公式ページ

Homebrew公式ページにアクセスし、下記のコマンドをcopyします。公式ページでも「このスクリプトをターミナルに貼り付け実行して下さい。」と丁寧にも記載してくれています。

/usr/bin/ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)"

インストールの実行

実行するとダウンロードとインストールが開始します。途中でEnterキーの押下を指示されるので、押します。

MacBook-Pro:tools mgr206$ /usr/bin/ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)"
==> This script will install:
/usr/local/bin/brew
/usr/local/share/doc/homebrew
/usr/local/share/man/man1/brew.1
/usr/local/share/zsh/site-functions/_brew
/usr/local/etc/bash_completion.d/brew
/usr/local/Homebrew
==> The following existing directories will be made group writable:
/usr/local/bin
==> The following existing directories will have their owner set to mgr206:
/usr/local/bin
==> The following existing directories will have their group set to admin:
/usr/local/bin
==> The following new directories will be created:
/usr/local/Cellar
/usr/local/Homebrew
/usr/local/Frameworks
/usr/local/etc
/usr/local/include
/usr/local/lib
/usr/local/opt
/usr/local/sbin
/usr/local/share
/usr/local/share/zsh
/usr/local/share/zsh/site-functions
/usr/local/var

Press RETURN to continue or any other key to abort
==> /usr/bin/sudo /bin/chmod u+rwx /usr/local/bin
==> /usr/bin/sudo /bin/chmod g+rwx /usr/local/bin
==> /usr/bin/sudo /usr/sbin/chown mgr206 /usr/local/bin
==> /usr/bin/sudo /usr/bin/chgrp admin /usr/local/bin
==> /usr/bin/sudo /bin/mkdir -p /usr/local/Cellar /usr/local/Homebrew /usr/local/Frameworks /usr/local/etc /usr/local/include /usr/local/lib /usr/local/opt /usr/local/sbin /usr/local/share /usr/local/share/zsh /usr/local/share/zsh/site-functions /usr/local/var
==> /usr/bin/sudo /bin/chmod g+rwx /usr/local/Cellar /usr/local/Homebrew /usr/local/Frameworks /usr/local/etc /usr/local/include /usr/local/lib /usr/local/opt /usr/local/sbin /usr/local/share /usr/local/share/zsh /usr/local/share/zsh/site-functions /usr/local/var
==> /usr/bin/sudo /bin/chmod 755 /usr/local/share/zsh /usr/local/share/zsh/site-functions
==> /usr/bin/sudo /usr/sbin/chown mgr206 /usr/local/Cellar /usr/local/Homebrew /usr/local/Frameworks /usr/local/etc /usr/local/include /usr/local/lib /usr/local/opt /usr/local/sbin /usr/local/share /usr/local/share/zsh /usr/local/share/zsh/site-functions /usr/local/var
==> /usr/bin/sudo /usr/bin/chgrp admin /usr/local/Cellar /usr/local/Homebrew /usr/local/Frameworks /usr/local/etc /usr/local/include /usr/local/lib /usr/local/opt /usr/local/sbin /usr/local/share /usr/local/share/zsh /usr/local/share/zsh/site-functions /usr/local/var
==> /usr/bin/sudo /bin/mkdir -p /Users/mgr206/Library/Caches/Homebrew
==> /usr/bin/sudo /bin/chmod g+rwx /Users/mgr206/Library/Caches/Homebrew
==> /usr/bin/sudo /usr/sbin/chown mgr206 /Users/mgr206/Library/Caches/Homebrew
==> /usr/bin/sudo /bin/mkdir -p /Library/Caches/Homebrew
==> /usr/bin/sudo /bin/chmod g+rwx /Library/Caches/Homebrew
==> /usr/bin/sudo /usr/sbin/chown mgr206 /Library/Caches/Homebrew
==> Downloading and installing Homebrew...
remote: Counting objects: 100655, done.
remote: Total 100655 (delta 0), reused 0 (delta 0), pack-reused 100655
Receiving objects: 100% (100655/100655), 22.95 MiB | 2.75 MiB/s, done.
Resolving deltas: 100% (73308/73308), done.
From https://github.com/Homebrew/brew
 * [new branch]          master     -> origin/master
 * [new tag]             0.1        -> 0.1
 * [new tag]             0.2        -> 0.2
 * [new tag]             0.3        -> 0.3
 * [new tag]             0.4        -> 0.4
 * [new tag]             0.5        -> 0.5
 * [new tag]             0.6        -> 0.6
 * [new tag]             0.7        -> 0.7
 * [new tag]             0.7.1      -> 0.7.1
 * [new tag]             0.8        -> 0.8
 * [new tag]             0.8.1      -> 0.8.1
 * [new tag]             0.9        -> 0.9
 * [new tag]             0.9.1      -> 0.9.1
 * [new tag]             0.9.2      -> 0.9.2
 * [new tag]             0.9.3      -> 0.9.3
 * [new tag]             0.9.4      -> 0.9.4
 * [new tag]             0.9.5      -> 0.9.5
 * [new tag]             0.9.8      -> 0.9.8
 * [new tag]             0.9.9      -> 0.9.9
 * [new tag]             1.0.0      -> 1.0.0
 * [new tag]             1.0.1      -> 1.0.1
 * [new tag]             1.0.2      -> 1.0.2
 * [new tag]             1.0.3      -> 1.0.3
 * [new tag]             1.0.4      -> 1.0.4
 * [new tag]             1.0.5      -> 1.0.5
 * [new tag]             1.0.6      -> 1.0.6
 * [new tag]             1.0.7      -> 1.0.7
 * [new tag]             1.0.8      -> 1.0.8
 * [new tag]             1.0.9      -> 1.0.9
 * [new tag]             1.1.0      -> 1.1.0
 * [new tag]             1.1.1      -> 1.1.1
 * [new tag]             1.1.10     -> 1.1.10
 * [new tag]             1.1.11     -> 1.1.11
 * [new tag]             1.1.12     -> 1.1.12
 * [new tag]             1.1.13     -> 1.1.13
 * [new tag]             1.1.2      -> 1.1.2
 * [new tag]             1.1.3      -> 1.1.3
 * [new tag]             1.1.4      -> 1.1.4
 * [new tag]             1.1.5      -> 1.1.5
 * [new tag]             1.1.6      -> 1.1.6
 * [new tag]             1.1.7      -> 1.1.7
 * [new tag]             1.1.8      -> 1.1.8
 * [new tag]             1.1.9      -> 1.1.9
 * [new tag]             1.2.0      -> 1.2.0
 * [new tag]             1.2.1      -> 1.2.1
 * [new tag]             1.2.2      -> 1.2.2
 * [new tag]             1.2.3      -> 1.2.3
 * [new tag]             1.2.4      -> 1.2.4
 * [new tag]             1.2.5      -> 1.2.5
 * [new tag]             1.2.6      -> 1.2.6
 * [new tag]             1.3.0      -> 1.3.0
 * [new tag]             1.3.1      -> 1.3.1
 * [new tag]             1.3.2      -> 1.3.2
 * [new tag]             1.3.3      -> 1.3.3
 * [new tag]             1.3.4      -> 1.3.4
 * [new tag]             1.3.5      -> 1.3.5
 * [new tag]             1.3.6      -> 1.3.6
 * [new tag]             1.3.7      -> 1.3.7
 * [new tag]             1.3.8      -> 1.3.8
 * [new tag]             1.3.9      -> 1.3.9
 * [new tag]             1.4.0      -> 1.4.0
 * [new tag]             1.4.1      -> 1.4.1
 * [new tag]             1.4.2      -> 1.4.2
 * [new tag]             1.4.3      -> 1.4.3
 * [new tag]             1.5.0      -> 1.5.0
 * [new tag]             1.5.1      -> 1.5.1
 * [new tag]             1.5.10     -> 1.5.10
 * [new tag]             1.5.11     -> 1.5.11
 * [new tag]             1.5.12     -> 1.5.12
 * [new tag]             1.5.13     -> 1.5.13
 * [new tag]             1.5.14     -> 1.5.14
 * [new tag]             1.5.2      -> 1.5.2
 * [new tag]             1.5.3      -> 1.5.3
 * [new tag]             1.5.4      -> 1.5.4
 * [new tag]             1.5.5      -> 1.5.5
 * [new tag]             1.5.6      -> 1.5.6
 * [new tag]             1.5.7      -> 1.5.7
 * [new tag]             1.5.8      -> 1.5.8
 * [new tag]             1.5.9      -> 1.5.9
 * [new tag]             1.6.0      -> 1.6.0
 * [new tag]             1.6.1      -> 1.6.1
 * [new tag]             1.6.2      -> 1.6.2
 * [new tag]             1.6.3      -> 1.6.3
HEAD is now at d14d0c25d Merge pull request #4143 from MikeMcQuaid/portable-ruby-2.3.3_2
==> Downloading https://homebrew.bintray.com/bottles-portable-ruby/portable-ruby-2.3.3_2.leopard_64.bottle.tar.gz
######################################################################## 100.0%
==> Pouring portable-ruby-2.3.3_2.leopard_64.bottle.tar.gz
==> Tapping homebrew/core
Cloning into '/usr/local/Homebrew/Library/Taps/homebrew/homebrew-core'...
remote: Counting objects: 4744, done.
remote: Compressing objects: 100% (4540/4540), done.
remote: Total 4744 (delta 55), reused 615 (delta 17), pack-reused 0
Receiving objects: 100% (4744/4744), 3.84 MiB | 1.19 MiB/s, done.
Resolving deltas: 100% (55/55), done.
Tapped 4540 formulae (4,786 files, 12MB)
==> Cleaning up /Library/Caches/Homebrew...
==> Migrating /Library/Caches/Homebrew to /Users/mgr206/Library/Caches/Homebrew...
==> Deleting /Library/Caches/Homebrew...
Already up-to-date.
==> Installation successful!

==> Homebrew has enabled anonymous aggregate user behaviour analytics.
Read the analytics documentation (and how to opt-out) here:
  https://docs.brew.sh/Analytics.html

==> Next steps:
- Run `brew help` to get started
- Further documentation: 
    https://docs.brew.sh

はい、これでインンストールは完了です。

opensslのアップデート

MacBook Proのopensslのバージョンが古すぎて色々と問題が起きて来たので更新します。

MacBook-Pro:tools mgr206$ brew install openssl
==> Downloading https://homebrew.bintray.com/bottles/openssl-1.0.2o_1.sierra.bottle.tar.gz
######################################################################## 100.0%
==> Pouring openssl-1.0.2o_1.sierra.bottle.tar.gz
==> Caveats
A CA file has been bootstrapped using certificates from the SystemRoots
keychain. To add additional certificates (e.g. the certificates added in
the System keychain), place .pem files in
  /usr/local/etc/openssl/certs

and run
  /usr/local/opt/openssl/bin/c_rehash

This formula is keg-only, which means it was not symlinked into /usr/local,
because Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries.

If you need to have this software first in your PATH run:
  echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile

For compilers to find this software you may need to set:
    LDFLAGS:  -L/usr/local/opt/openssl/lib
    CPPFLAGS: -I/usr/local/opt/openssl/include

==> Summary
🍺  /usr/local/Cellar/openssl/1.0.2o_1: 1,791 files, 12.3MB
MacBook-Pro:tools mgr206$ openssl version
OpenSSL 0.9.8zh 14 Jan 2016

バージョンアップ失敗?

インストール後にバージョンを確認すると、0.9.8zhで変わっていません。

MacBook-Pro:bin mgr206$ which openssl
/usr/bin/openssl

brewでopensslをインストールしたので確認してみます。

MacBook-Pro:bin mgr206$ which openssl
/usr/bin/openssl
MacBook-Pro:bin mgr206$ brew list openssl
/usr/local/Cellar/openssl/1.0.2o_1/.bottle/etc/ (8 files)
/usr/local/Cellar/openssl/1.0.2o_1/bin/c_rehash
/usr/local/Cellar/openssl/1.0.2o_1/bin/openssl
/usr/local/Cellar/openssl/1.0.2o_1/include/openssl/ (74 files)
/usr/local/Cellar/openssl/1.0.2o_1/lib/libcrypto.1.0.0.dylib
/usr/local/Cellar/openssl/1.0.2o_1/lib/libssl.1.0.0.dylib
/usr/local/Cellar/openssl/1.0.2o_1/lib/engines/ (12 files)
/usr/local/Cellar/openssl/1.0.2o_1/lib/pkgconfig/ (3 files)
/usr/local/Cellar/openssl/1.0.2o_1/lib/ (4 other files)
/usr/local/Cellar/openssl/1.0.2o_1/share/man/ (1680 files)

PATHの修正

webで調べると、$brew link opensslでリンクする、という記事もありましたが自分の環境ではエラーになりました。

MacBook-Pro:/ mgr206$ brew link openssl --force
Warning: Refusing to link: openssl
Linking keg-only openssl means you may end up linking against the insecure,
deprecated system OpenSSL while using the headers from Homebrew's openssl.
Instead, pass the full include/library paths to your compiler e.g.:
  -I/usr/local/opt/openssl/include -L/usr/local/opt/openssl/lib

そこで.bash_profileにPATHを設定します。PATHは/usr/local/opt/openssl/binです。
.bash_profileがなかったので作成します。

MacBook-Pro:/ mgr206$ sudo touch .bash_profile
Password:
MacBook-Pro:/ mgr206$ ls -la
・
・
-rw-r--r--   1 root        wheel         0  5  3 20:57 .bash_profile
・
・

ファイルができたのでPATHを設定します。

MacBook-Pro:/ mgr206$ echo 'export PATH=/usr/local/opt/openssl/bin:$PATH' >> ~/.bash_profile
MacBook-Pro:/ mgr206$ source .bash_profile

確認

brewでインストールしたopensslのPATHとバージョンになっています。

MacBook-Pro:/ mgr206$ which openssl
/usr/local/opt/openssl/bin/openssl
MacBook-Pro:/ mgr206$ openssl version
OpenSSL 1.0.2o  27 Mar 2018

Register as a new user and use Qiita more conveniently

  1. You get articles that match your needs
  2. You can efficiently read back useful information
  3. You can use dark theme
What you can do with signing up
13