Methanol → Methyl 2-bromo-5-methylbenzoate

HRID 1435766Notes

Reaction equation

HRID 1435766 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[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]([CH3:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 2280802-Bromo-5-methylbenzoic acid

Product 1

HCID 15110996Methyl 2-bromo-5-methylbenzoateYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-bromo-5-methyl-benzoic acid (3.0 g, 14 mmol) in dichloromethane (100 ml) was added a solution of oxalyl chloride in dichloromethane (2 M, 8 ml, 16 mmol) followed by N,N-dimethylformamide (5 drops). After stirring for 30 minutes, methanol (15 ml) was added. After stirring for 3 hours, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 ml) and saturated aqueous potassium carbonate solution (100 ml). The organic layer was concentrated under reduced pressure to provide methyl 2-bromo-5-methyl-benzoate (3.2 g, 99% yield).

Workup

  1. stirringAfter stirring for 3 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (200 ml) and saturated aqueous potassium carbonate solution (100 ml)
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3e73fdbc3709482490aef7a11a7eeae0
Source dataset
uspto-grants-2009_11
Patent number
US07618968B2

Reaction notes

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