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

HRID 2194865Notes

Reaction equation

HRID 2194865 reaction equation
[BrH:1].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]O)=[C:5]([CH3:11])[CH:4]=1>C(O)(=O)C.O>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][Br:1])=[C:5]([CH3:11])[CH:4]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 22280088(4-Bromo-2-methylphenyl)methanol

Product 1

HCID 225690184-Bromo-1-(bromomethyl)-2-methylbenzene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Hydrobromic acid (conc., 2 eq.) was added to a stirred solution of the alcohol from step 1 (1 eq.) in acetic acid (0.22M). The mixture was stirred at 50° C. for 12 h, cooled down to room temperature, poured in water and extracted with Et2O. The organic extract was washed with water, aqueous sodium hydrogen carbonate (3×), brine, dried over MgSO4, filtered and concentrated to afford the desired benzyl bromide as a light yellow solid.

Workup

  1. temperaturecooled down to room temperature
  2. extractionextracted with Et2O
  3. extractionThe organic extract
  4. washwas washed with water, aqueous sodium hydrogen carbonate (3×), brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3deaf2696e65401383fd420096b49c58
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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