Methanol → Methyl 2-chloro-3-nitrobenzoate

HRID 1698527Notes

Reaction equation

HRID 1698527 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14]N(C)C=O.C(Cl)(=O)C(Cl)=O.CO>ClCCl>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 198702-Chloro-3-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 10751184Methyl 2-chloro-3-nitrobenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of 20 g (99 mmol) of 2-chloro-3-nitrobenzoic acid in 800 mL dichloromethane was cooled in an ice bath. Dimethylformamide (0.40 mL) was added to the reaction followed by drop wise addition of 13.85 g (109 mmol) of oxalyl chloride. The reaction was allowed to warm to room temperature and was stirred for 6 h. Methanol (200 mL) was added drop wise and the reaction was stirred overnight. The reaction was concentrated to a residue, dissolved in dichloromethane and passed through a plug of silica eluting with a 50% ethyl acetate/hexane mixture. The filtrate was concentrated in vacuo to give 21.5 g (100%) of the title compound.

Workup

  1. stirringthe reaction was stirred overnight
  2. concentrationThe reaction was concentrated to a residue
  3. dissolutiondissolved in dichloromethane
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7e81a8c3b90e4fafbd8895e898a3b397
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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