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

HRID 906318Notes

Reaction equation

HRID 906318 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

A solution of 1-[3,5-bis(trifluoromethyl)phenyl]ethanol (500 mg, 1.94 mmol) in toluene (5 mL) was added with phosphorus tribromide (550.0 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 (257.9 mg, 41%) as 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-2a05a7544cbb45cca810f329c9a5685a
Source dataset
uspto-grants-2011_09
Patent number
US08012989B2

Reaction notes

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