Dimethylformamide → Methyl 3-(chlorocarbonyl)benzoate

HRID 926784Notes

Reaction equation

HRID 926784 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)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Into a 250-mL round bottom flask, was placed a solution of 3-(methoxycarbonyl)benzoic acid (6.2 g, 34.44 mmol, 1.00 equiv) in dichloromethane (50 mL), oxalyl dichloride (8.74 g, 69.37 mmol, 2.00 equiv), and N,N-dimethylformamide (cat.). The resulting solution was stirred for 1 h at 40° C. in an oil bath. The resulting mixture was concentrated under vacuum. This resulted in 6.6 g (87%) of methyl 3-(chlorocarbonyl)benzoate as brown oil.

Workup

  1. customInto a 250-mL round bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 6.6 g (87%) of methyl 3-(chlorocarbonyl)benzoate as brown oil

Sources & evidence

ORD record
ord-6c0409c500cd4168b1268433c60e93dc
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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