Methanol → Methyl 2-Bromo-5-chlorobenzoate

HRID 1591630Notes

Reaction equation

HRID 1591630 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](Cl)(=O)C(Cl)=O.CO>ClCCl.CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 890272-Bromo-5-chlorobenzoic acid

Product 1

HCID 280500Methyl 2-Bromo-5-chlorobenzoateYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-bromo-5-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. After stirring for 3 hours, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (150 ml) and saturated aqueous potassium carbonate solution (100 ml). The organic layer was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (1:2) to provide methyl 2-bromo-5-chloro-benzoate (2.1 g, 79% yield).

Workup

  1. stirringAfter stirring for 3 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (150 ml) and saturated aqueous potassium carbonate solution (100 ml)
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (1:2)

Sources & evidence

ORD record
ord-b727a72b76b442aeb3a194adf39f1302
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Reaction notes

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