Methyl 4-methylbenzoate → Methyl 4-(bromomethyl)benzoate

HRID 615490Notes

Reaction equation

HRID 615490 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Br:12]Br>C(Cl)(Cl)(Cl)Cl.[W]>[Br:12][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7455Methyl 4-methylbenzoateHCID 24408Bromine

Product 1

HCID 256687Methyl 4-(bromomethyl)benzoateYield 97%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 15.0 g (0.1 mole) of methyl 4-methylbenzoate in 150 ml of carbon tetrachloride was stirred and heated to reflux with a 350 watt tungsten lamp. A solution of 16.0 g (0.1 mole) of bromine in 150 ml of carbon tetrachloride was added over 3 minutes by an addition funnel. The colorless reaction mixture was evaporated to give 22.03 g (97% yield) of the title compound as colorless prisms.

Workup

  1. temperatureheated
  2. customThe colorless reaction mixture was evaporated

Sources & evidence

ORD record
ord-b68deafe32ab4615a63b9e8ff9d7556e
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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