Methanol → Methyl 2-(bromomethyl)-6-methylbenzoate

HRID 1717442Notes

Reaction equation

HRID 1717442 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:4]=1[C:5](Br)=[O:6].[CH3:13][OH:14]>CCCCCCC>[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:4]=1[C:5]([O:14][CH3:13])=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 219803072-(Bromomethyl)-6-methylbenzoyl bromide

Product 1

HCID 10263795Methyl 2-(bromomethyl)-6-methylbenzoateYield 98.8%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

200 g (240 mmol) of 2-bromomethyl-6-methylbenzoyl bromide solution (35% solution in heptane) are added to 400 ml of methanol. After stirring at RT for one hour, 400 ml of n-heptane are added. The solution is washed successively with 600 ml of sat. sodium hydrogencarbonate solution and three times with 200 ml each time of water. Subsequently, the solvent is removed fully under reduced pressure. 98.8% of methyl 2-bromomethyl-6-methylbenzoate is obtained as a colorless oil having a purity of 80% (included in the yield) and having a molecular weight of 241.99 (C10H11BrO2); MS (ESI): 243.1 [M+H+].

Workup

  1. washThe solution is washed successively with 600 ml of sat. sodium hydrogencarbonate solution and three times with 200 ml each time of water
  2. customSubsequently, the solvent is removed fully under reduced pressure

Sources & evidence

ORD record
ord-a454f6bc4218401bb442a2697f33111c
Source dataset
uspto-grants-2010_09
Patent number
US07803950B2

Reaction notes

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