5-Chloro-2-nitrobenzoic acid → 5-Chloro-2-nitrobenzoyl chloride

HRID 844139Notes

Reaction equation

HRID 844139 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)(=O)C([Cl:17])=O>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([Cl:17])=[O:8]

Participants

5

Reactant 2

HCID 172865-Chloro-2-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 27236855-Chloro-2-nitrobenzoyl chlorideYield 104.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-chloro-2-nitrobenzoic acid (21 g, 100 mmol) in dry methylene chloride (200 mL) at 0° C. were added several drops of DMF, followed by oxalyl chloride (13 mL, 150 mmol). The reaction was warmed to ambient temperature. After 16 hours the solvents were removed and the viscous oil dried in vacuo to afford 23 g (quantitative yield) of 5-chloro-2-nitrobenzoyl chloride; NMR (CDCl3) 8.1 (d, 1), 7.7 (m, 2) ppm.

Workup

  1. customAfter 16 hours the solvents were removed
  2. customthe viscous oil dried in vacuo

Sources & evidence

ORD record
ord-87386d6513a149b9ac529799d38d7708
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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