Dichloromethane → Methyl 2,4-dichloro-6-methylbenzoate

HRID 2427749Notes

Reaction equation

HRID 2427749 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([CH3:10])=[CH:8][C:7](Br)=[CH:6][C:5]=1[Cl:12].[Cl:14]CCl>CN(C=O)C.Cl[Cu]>[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([Cl:14])=[CH:6][C:5]=1[Cl:12]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 45480505Methyl 4-bromo-2-chloro-6-methylbenzoate

Product 1

HCID 57949430Methyl 2,4-dichloro-6-methylbenzoateYield 65%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A solution of the 4-bromo-2-chloro-6-methyl-benzoic acid methyl ester (1.31 g, 5 mmol) in DMF was treated with CuCl (1.96 g, 20 mmol) and stirred at 140° C. for 1-2 h. After this time, the reaction mixture was diluted with dichloromethane (15 mL) and the solids removed by filtration. The filtrate was concentrated. Silica gel column chromatography using, typically 30% ethyl acetate in hexane, afforded 2,4-dichloro-6-methyl-benzoic acid methyl ester (0.72 g, 65%).

Workup

  1. customthe solids removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-718a85a4f2824feab158b3241790722b
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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