Methyl iodide → Methyl 2-bromo-5-methoxy-4-methylbenzoate

HRID 615500Notes

Reaction equation

HRID 615500 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([OH:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:14]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([O:13][CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20428674Methyl 2-bromo-5-hydroxy-4-methylbenzoate

Product 1

HCID 20428669Methyl 2-bromo-5-methoxy-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 800 mg of material from step b. 10 ml of dry reagent grade acetone, 456 mg of K2CO3, and excess methyl iodide was stirred a refluxed for 3 days. Ether extraction provided the ester in a form suitable for further transformation.

Workup

  1. temperaturea refluxed for 3 days
  2. extractionEther extraction

Sources & evidence

ORD record
ord-0cae458202b4474b925d7ed95f4d2d05
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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