4-Chloro-3-nitrobenzoic acid → 4-Chloro-3-nitrobenzoyl chloride

HRID 2399720Notes

Reaction equation

HRID 2399720 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(Cl)(=O)C([Cl:17])=O>CN(C=O)C.ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:17])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 73204-Chloro-3-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 1234774-Chloro-3-nitrobenzoyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
30 °C

Procedure

To a stirred suspension of 4-chloro-3-nitrobenzoic acid (20 g) in DMF (1 cm3) and dichloromethane (100 cm3) was added oxalyl chloride (13 g) in dichloromethane (50 cm3) over 1 hour. The reaction was stirred at 30° C. for 5 hours, after which reaction became homogeneous, and stirred at the ambient temperature for 18 hours. Evaporation under reduced pressure gave a white solid that was triturated with hexane and dried to give 4-chloro-3-nitrobenzoyl chloride as a white solid (21.82 g). 1H nmr (CDCl3) d: 8.61 (1H, d), 8.26 (1H, dd), 7.78 (1H, d). Mpt 49°-51° C.

Workup

  1. customafter which reaction
  2. stirringstirred at the ambient temperature for 18 hours
  3. customEvaporation under reduced pressure
  4. customgave a white solid
  5. customthat was triturated with hexane
  6. customdried

Sources & evidence

ORD record
ord-c1745beb9b0b4b9da30b0f12b1737f30
Source dataset
uspto-grants-1995_09
Patent number
US05451594

Reaction notes

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