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

HRID 1857874노트

반응식

HRID 1857874 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 106321513-Tert-butyl-4-methoxyphenylboronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4af5cce2f8fe4956a54a31f830be2da6
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147255

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