Methanol → Methyl 5-bromo-2-chlorobenzoate

HRID 1591617Notes

Reaction equation

HRID 1591617 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-37cbd43736b94d348c09fd19a11e55af
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Reaction notes

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