Dimethylformamide → Methyl 3-(chlorocarbonyl)benzoate

HRID 2409805Notes

Reaction equation

HRID 2409805 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])=[O:4].C(Cl)(=O)C([Cl:17])=O.CN(C)C=O>ClCCl>[Cl:17][C:8]([C:7]1[CH:6]=[C:5]([CH:13]=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 6018803-(Methoxycarbonyl)benzoic acid

Product 1

HCID 15563901Methyl 3-(chlorocarbonyl)benzoateYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To 3-(methoxycarbonyl)benzoic acid (6.2 g, 34.44 mmol, 1.00 equiv) in dichloromethane (50 mL) was added oxalyl dichloride (8.74 g, 69.37 mmol, 2.00 equiv) and N,N-dimethylformamide (cat.) and the resulting solution was stirred for 1 h at 40° C. in an oil bath. The mixture was concentrated under vacuum to yield 6.6 g (87%) of methyl 3-(chlorocarbonyl)benzoate as brown oil.

Workup

  1. concentrationThe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-b350c393e6cf4b9e9f2a031620a3305b
Source dataset
uspto-grants-2014_08
Patent number
US08815910B2

Reaction notes

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