Water → (R)-3-(1,1,1-trifluoropropan-2-yloxy)phenyl boronic acid

HRID 83545ノート

反応式

HRID 83545 の反応式
[F:1][C:2]([F:7])([F:6])[C@H:3]([OH:5])[CH3:4].[H-].[Na+].BrC[C:12]1[CH:13]=[C:14]([B:18]([OH:20])[OH:19])[CH:15]=[CH:16][CH:17]=1.O>CN(C)C=O>[F:1][C:2]([F:7])([F:6])[C@H:3]([O:5][C:12]1[CH:13]=[C:14]([B:18]([OH:20])[OH:19])[CH:15]=[CH:16][CH:17]=1)[CH3:4]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27732813-(Bromomethyl)benzeneboronic acidHCID 6993809(2R)-1,1,1-trifluoropropan-2-ol

生成物 1

HCID 86680377(R)-3-(1,1,1-trifluoropropan-2-yloxy)phenyl boronic acid収率 135%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of (R)-1,1,1-trifluoropropan-2-ol (212 mg) in N,N-dimethylformamide (1.5 ml) was cooled to 0° C., sodium hydride (74 mg, 60 wt. % oil dispersion) and 3-(bromomethyl)phenyl boronic acid (100 mg) were sequentially added thereto, and the mixture was stirred at room temperature for 2 hours. To this reaction mixture were added water and an 1M aqueous solution of hydrochloric acid, and the mixture was extracted with ethyl acetate. This organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give the titled compound (147 mg).

後処理

  1. extractionan 1M aqueous solution of hydrochloric acid, and the mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-afbdef5befde4ed5b658e837c2033db6
出典データセット
uspto-grants-2014_09
特許番号
US08846746B2

反応ノート

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