Hydrogen Bromide → 4-(2-Bromoethyl)-1,2-difluorobenzene

HRID 1992375Notes

Reaction equation

HRID 1992375 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10]O)[CH:5]=[CH:6][C:7]=1[F:8].[BrH:12]>C(O)(=O)C.S(=O)(=O)(O)O>[Br:12][CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 27583132-(3,4-Difluorophenyl)ethan-1-ol

Product 1

HCID 150200534-(2-Bromoethyl)-1,2-difluorobenzeneYield 25.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(3,4-difluoro-phenyl)-ethanol (5 g, 0.032 mol, from step (iii) above), 51.84 ml (49%, 0.64 mol) of HBr in acetic acid and 5 ml of sulfuric acid was stirred at 100° C. for 4 h. The reaction mixture was poured into ice and extracted with diethylether. Organic layer was washed with NaHCO3, water and dried over sodium sulfate. Solvent evaporation under reduced pressure followed by purification (three times) over silica gel using petroleum ether as eluent afforded (1.8 g) of the title compound as a liquid.

Workup

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

Sources & evidence

ORD record
ord-71f62502cb6b458597071ddcd1d37bac
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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