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

HRID 83545Notes

Reaction equation

HRID 83545 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-afbdef5befde4ed5b658e837c2033db6
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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