Water → 1-Chloro-3-(2,2,2-trifluoro-1,1-dimethylethoxymethyl)benzene

HRID 83557

Reaction equation

HRID 83557 reaction equation
[H-].[Na+].[F:3][C:4]([F:10])([F:9])[C:5]([CH3:8])([OH:7])[CH3:6].Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1.O>CN(C)C=O>[Cl:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][O:7][C:5]([CH3:8])([CH3:6])[C:4]([F:10])([F:9])[F:3])[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 681821,1,1-Trifluoro-2-methylpropan-2-olHCID 698381-(Bromomethyl)-3-chlorobenzene

Product 1

HCID 712877591-Chloro-3-(2,2,2-trifluoro-1,1-dimethylethoxymethyl)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension cooled to 0° C. of sodium hydride (126 mg, 60 wt. % oil dispersion) in N,N-dimethylformamide (5 ml) was added dropwise, 1,1,1-trifluoro-2-methylpropan-2-ol (320 μL) under argon atmosphere, and the mixture was stirred for 15 minutes. To this reaction mixture was added dropwise 1-bromomethyl-3-chlorobenzene (320 μL), and the mixture was stirred for 3 hours. To this reaction mixture was added water, 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. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 40/1) to give the titled compound (389 mg).

Workup

  1. additionwas added dropwise
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThis organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 40/1)

Sources & evidence

ORD record
ord-8fa502f875ea4986a76c1d68f92ecf39
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Linked notes

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