Phosphorus tribromide → 1-(1-Bromoethyl)-3,5-bis(trifluoromethyl)benzene

HRID 1442512Notes

Reaction equation

HRID 1442512 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:13](O)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.P(Br)(Br)[Br:19]>C1(C)C=CC=CC=1.O>[Br:19][CH:13]([C:5]1[CH:4]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=1)[CH3:14]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 64257391-(3,5-Bis(trifluoromethyl)phenyl)ethanol

Product 1

HCID 129473971-(1-Bromoethyl)-3,5-bis(trifluoromethyl)benzeneYield 41.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1-[3,5-bis(trifluoromethyl)phenyl]ethanol (500 mg, 1.94 mmol) in toluene (5 mL) was added phosphorus tribromide (550 mg, 2.03 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane (258 mg, 41%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-9338fa46bcc04b82b3d31801c1ec905c
Source dataset
uspto-grants-2010_02
Patent number
US07659271B2

Reaction notes

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