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

HRID 1027239ノート

反応式

HRID 1027239 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 867106184-Benzyloxy-2-(trifluoromethoxy)phenylboronic acid収率 135.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-225159859b19461c93f562a0e1dbbd20
出典データセット
uspto-grants-2014_05
特許番号
US08729263B2

反応ノート

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