Methanol → Methyl 5-bromo-2-chlorobenzoate

HRID 1435748Notes

Reaction equation

HRID 1435748 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:12](Cl)(=O)C(Cl)=O.CO>ClCCl.CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:12])=[O:8]

Participants

6

Reactant 3

HCID 887MethanolHCID 331275-Bromo-2-chlorobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 842098Methyl 5-bromo-2-chlorobenzoateYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 5-bromo-2-chloro-benzoic acid (2.5 g, 10.6 mmol) in dichloromethane (50 ml) was added a solution of oxalyl chloride in dichloromethane (2 M, 6 ml, 12 mmol) followed by N,N-dimethylformamide (5 drops). After stirring for 30 minutes, methanol (10 ml) was added and the mixture was stirred for 20 hours. The mixture was concentrated under reduced pressure and partitioned between ethyl acetate (150 ml) and saturated aqueous potassium carbonate solution (100 ml). The organic layer was concentrated under reduced pressure to provide methyl 5-bromo-2-chloro-benzoate (2.4 g, 91% yield).

Workup

  1. stirringthe mixture was stirred for 20 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. custompartitioned between ethyl acetate (150 ml) and saturated aqueous potassium carbonate solution (100 ml)
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5a6ac5b12b2b45eaa00caa6dd1514ea7
Source dataset
uspto-grants-2009_11
Patent number
US07618968B2

Reaction notes

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