Ammonia → Methyl 4-(bromomethyl)benzoate

HRID 2081764Notes

Reaction equation

HRID 2081764 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.ClCCl.P(Br)(Br)[Br:17].N>O>[Br:17][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 24614Phosphorus tribromideHCID 81325Methyl 4-(hydroxymethyl)benzoate

Product 1

HCID 256687Methyl 4-(bromomethyl)benzoateYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

11.5 g (70 mmol) of methyl 4-hydroxymethylbenzoate are added to 120 ml of dichloromethane and 47.3 ml of phosphorus tribromide are added thereto. The mixture is stirred for one hour at ambient temperature and a semi-concentrated solution of ammonia in water is carefully added, whilst cooling with ice, until a pH of 8 to 9 is achieved. The organic phase is separated off and dried and the solvent is distilled off. 13.4 g (84% of theory) of the methyl 4-bromomethylbenzoate are obtained (analogously to Compound 6).

Workup

  1. additionare added
  2. temperaturewhilst cooling with ice, until a pH of 8 to 9
  3. customThe organic phase is separated off
  4. customdried
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-ae33ca85de1d4fdaaa9b222d1492d01c
Source dataset
uspto-grants-1993_02
Patent number
US05185442

Reaction notes

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