Hydrochloric Acid → 3-Tert-butyl-4-methoxyphenylboronic acid

HRID 1057955ノート

反応式

HRID 1057955 の反応式
[C:1]([C:5]1[CH:6]=[C:7](Br)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[B:19](OC)([O:22]C)[O:20]C.Cl>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([B:19]([OH:22])[OH:20])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 37338984-Bromo-2-tert-butyl-1-methoxybenzeneHCID 178418339Butyllithium

生成物 1

HCID 106321513-Tert-butyl-4-methoxyphenylboronic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4 g (16.5 mmol) of 3-tert-butyl-4-methoxybromobenzene and 50 ml of THF are introduced into a three-necked flask under a stream of nitrogen. 7.9 ml (19.8 mmol) of n-butyllithium (2.5 M in hexane) are added dropwise at −78° C., the mixture is stirred for 15 minutes at this temperature, 5.6 ml (49.5 mmol) of trimethyl borate are added and the mixture is stirred for 2 hours. 20 ml of hydrochloric acid (1 N) are added at −50° C. and the mixture is allowed to return to room temperature. The reaction medium is extracted with ethyl ether and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. 3.79 g (100%) of the expected boronic acid are collected, which is used in its present state for the rest of the synthesis.

後処理

  1. additionare added
  2. customto return to room temperature
  3. extractionThe reaction medium is extracted with ethyl ether
  4. customthe organic phase is separated out after settling
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. custom3.79 g (100%) of the expected boronic acid are collected
  8. customwhich is used in its present state for the rest of the synthesis

出典と根拠

ORDレコード
ord-a7b1f47541cd4ec0b6bf8a8b72ec2320
出典データセット
uspto-grants-2003_02
特許番号
US06515021B1

反応ノート

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