Trimethyl borate → 4-Benzyloxy-2-(trifluoromethoxy)phenylboronic acid

HRID 1027239노트

반응식

HRID 1027239 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[C:11]([O:16][C:17]([F:20])([F:19])[F:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.C[O:27][B:28](OC)[O:29]C>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([B:28]([OH:29])[OH:27])=[C:11]([O:16][C:17]([F:20])([F:19])[F:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 8470Trimethyl borateHCID 672362364-(Benzyloxy)-1-bromo-2-(trifluoromethoxy)benzeneHCID 178418339Butyllithium

생성물 1

HCID 867106184-Benzyloxy-2-(trifluoromethoxy)phenylboronic acid수율 135.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a mixture of 4-(benzyloxy)-1-bromo-2-(trifluoromethoxy)benzene (1.8 g, 5.19 mmol) in THF (20 mL) was added butyllithium (2.5 M in THF, 2.28 mL, 5.70 mmol) at −78° C. dropwise over 10 minutes. The reaction mixture was stirred at −78° C. for 1 h, then trimethylborate (1.73 mL, 15.6 mmol) was added. The mixture was warmed to room temperature and stirred overnight. The mixture was concentrated from diethyl ether three times and the residue was dried on high vacuum to provide the title compound as a gummy solid (2.2 g, 61% pure, 83% yield). The crude material was carried on without further purification. MS (M−1)=311.3

후처리

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred overnight
  3. concentrationThe mixture was concentrated from diethyl ether three times
  4. customthe residue was dried on high vacuum

출처 및 근거

ORD 기록
ord-225159859b19461c93f562a0e1dbbd20
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729263B2

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