Water → Methyl 2-(bromomethyl)benzoate

HRID 868424Notes

Reaction equation

HRID 868424 reaction equation
O.[C:2]1([CH3:12])[C:3]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[Br:13]Br>C(Cl)(Cl)(Cl)Cl>[CH3:11][O:10][C:8](=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:12][Br:13]

Participants

5

Reactant 3

HCID 962WaterHCID 24408Bromine3×HCID 33094Methyl o-toluate

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A water jacketted, immersion photolysis vessel equipped with a N2 inlet, dropping funnel and a reflux condenser was charged with 1 L of carbon tetrachloride and 127 g. (0.847 mol) of 2-methyl toluate (Pfaltz and Bauer M29200). A solution of 400 ml carbon tetrachloride and 43.5 ml (0.849 mol) of bromine was added to the dropping funnel. After the solution had been heated to reflux the bromine solution was slowly added while the solution was irradiated with a 600 watt incandescent lamp. After the addition of the bromine solution was complete, the lamp was turned off and the solution cooled. The carbon tetrachloride was removed under reduced pressure. The resultant oil was crystallized from 250 ml of a (1:1) solution of diethyl ether and hexane. The solid was collected and washed with hexane to yield 119 g. (61%) of product.

Workup

  1. customimmersion photolysis vessel equipped with a N2 inlet
  2. temperatureAfter the solution had been heated
  3. additionwas slowly added while the solution
  4. customwas irradiated with a 600 watt incandescent lamp
  5. temperaturethe solution cooled
  6. customThe carbon tetrachloride was removed under reduced pressure
  7. customThe resultant oil was crystallized from 250 ml of a (1:1) solution of diethyl ether and hexane
  8. customThe solid was collected
  9. washwashed with hexane
  10. customto yield 119 g

Sources & evidence

ORD record
ord-044a85984e594d8794be40b60fc5928f
Source dataset
uspto-grants-1988_10
Patent number
US04778931

Reaction notes

Loading…