Dimethylformamide → 1-(1-Bromoethyl)-3-(trifluoromethyl)benzene

HRID 2052536Notes

Reaction equation

HRID 2052536 reaction equation
[Br:1]Br.[F:3][C:4]([F:15])([F:14])[C:5]1[CH:6]=[C:7]([CH:11](O)[CH3:12])[CH:8]=[CH:9][CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O>CCCCCC>[F:3][C:4]([F:15])([F:14])[C:5]1[CH:6]=[C:7]([CH:11]([Br:1])[CH3:12])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 24408Bromine2×HCID 1362961-(3-(Trifluoromethyl)phenyl)ethanol

Product 1

HCID 27756241-(1-Bromoethyl)-3-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

bromine (32.5 g≡10.4 ml) was added over 15 minutes to a stirred mixture of (±)-1-(3-trifluoromethylphenyl)-ethanol [38 g, described by Overberger et al., Org. Synth. Coll. 3, 200 (1955)], triphenylphosphine (56 g) and dry dimethylformamide (200 ml) in an atmosphere of nitrogen. The temperature of the mixture was maintained at 40°-50° C. by ice-cooling. Further bromine was added dropwise to give a permanent orange colour and after stirring for 15 minutes the mixture was poured into a mixture of ice-water (1 liter) and hexane (500 ml). The mixture was filtered and the solid material was washed well with hexane. The hexane solutions were combined, washed with water (4×100 ml), dried over sodium sulphate and distilled to give (±)-1-(3-trifluoromethylphenyl)ethyl bromide, b.p. 98°-105° C./15 mmHg, as a clear mobile oil.

Workup

  1. temperatureThe temperature of the mixture was maintained at 40°-50° C. by ice-
  2. temperaturecooling
  3. customto give a permanent orange colour
  4. filtrationThe mixture was filtered
  5. washthe solid material was washed well with hexane
  6. washwashed with water (4×100 ml)
  7. dry with materialdried over sodium sulphate
  8. distillationdistilled

Sources & evidence

ORD record
ord-47dece557f104bd18203dc965fcc4074
Source dataset
uspto-grants-1980_01
Patent number
US04185992

Reaction notes

Loading…