Bromine → 2-Bromo-3,5-dimethoxy-4-methyl-benzoic acid methyl ester

HRID 1692615Notes

Reaction equation

HRID 1692615 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=1.[Br:16]Br>ClCCl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:5]=[C:6]([O:13][CH3:14])[C:7]([CH3:12])=[C:8]([O:10][CH3:11])[C:9]=1[Br:16]

Participants

4

Reactant 2

HCID 24408BromineHCID 2747951Methyl 3,5-dimethoxy-4-methylbenzoate

Product 1

HCID 594024012-Bromo-3,5-dimethoxy-4-methyl-benzoic acid methyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,5-Dimethoxy-4-methyl-benzoic acid methyl ester (1 mmol) was taken in 2 mL of dichloromethane, and a solution of bromine (1 mmol) in 0.5 mL of dichloromethane was added from a pressure-equalizing dropping funnel at room temperature over a period of 1.5 h. A NaOH trap system was provided on top of the addition funnel. The mixture was then stirred for 5 h and the solvent was evaporated off to give 2-Bromo-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (95%).

Workup

  1. customat room temperature
  2. customof 1.5 h
  3. customA NaOH trap system was provided on top of the addition funnel
  4. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-c44a3593557c4eb9a03f679158886056
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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