Hydrogen Bromide → 1-(2-Bromoethyl)-4-(trifluoromethyl)benzene

HRID 1992384Notes

Reaction equation

HRID 1992384 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10]O)=[CH:5][CH:4]=1.[BrH:14]>C(O)(=O)C.S(=O)(=O)(O)O>[Br:14][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 112755102-(4-(Trifluoromethyl)phenyl)ethan-1-ol

Product 1

HCID 149499411-(2-Bromoethyl)-4-(trifluoromethyl)benzene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A mixture of step 2-(4-trifluoromethylphenyl)-ethanol (10 g, 0.053 mol, from step (iii) above), 86 ml (1.06 M) HBr in acetic acid and 10 ml sulfuric acid was stirred at 100° C. for 4 h. The reaction mixture was poured into ice and extracted with diethylether. The organic layer was washed with NaHCO3, water and dried over sodium sulfate. Solvent evaporation under reduced pressure followed by purification over silica gel using petroleum ether as eluent afforded 5 g of the title compound as a liquid.

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted with diethylether
  3. washThe organic layer was washed with NaHCO3, water
  4. dry with materialdried over sodium sulfate
  5. customSolvent evaporation under reduced pressure
  6. customfollowed by purification over silica gel

Sources & evidence

ORD record
ord-1bd13ad7135d44e494a3fa85b535c869
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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