Hydrogen Bromide → 4-Bromo-1-(bromomethyl)-2-chlorobenzene

HRID 1641531Notes

Reaction equation

HRID 1641531 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[C:4]([Cl:10])[CH:3]=1.C1(C)C=CC=CC=1.[BrH:18].O>C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][Br:18])=[C:4]([Cl:10])[CH:3]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 1140TolueneHCID 43805739(4-Bromo-2-chlorophenyl)methanol

Product 1

HCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 4-bromo-2-chlorobenzyl alcohol (399 g) of Reference Example 12 were added toluene (2452 mL) and 48% aqueous hydrogen bromide solution (2453 mL), and the mixture was refluxed with stirring for 2 hr. After cooling, water and ethyl acetate were added to the reaction mixture. After partitioning and extraction, the organic layer was washed with water, 1M aqueous sodium hydroxide solution and 25% brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (535 g) as a pale-yellow oil.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureAfter cooling
  3. customAfter partitioning
  4. extractionextraction
  5. washthe organic layer was washed with water, 1M aqueous sodium hydroxide solution and 25% brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d123d3a132ed4ad3be5ea1567e2e21de
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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