Dimethylformamide → 3-Fluoro-4-nitrobenzoyl chloride

HRID 1796308Notes

Reaction equation

HRID 1796308 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].C(Cl)(=O)C([Cl:17])=O.CN(C=O)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([Cl:17])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 27746563-Fluoro-4-nitrobenzoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of 3-fluoro-4-nitro-benzoic acid (4.0 g, 21.6 mmol) in anhydrous CH2Cl2 (200 mL) at 0° C. was slowly added oxalyl chloride (2.45 mL, 28.0 mmol) and a drop of DMF. The solution was stirred and allowed to warm to RT overnight before concentrating under reduced pressure to give 3 (4.39 g, 100%).

Workup

  1. customat 0° C.
  2. concentrationbefore concentrating under reduced pressure

Sources & evidence

ORD record
ord-1994f680e37d40a5b3cfe79cdba63d47
Source dataset
uspto-grants-2006_04
Patent number
US07030141B2

Reaction notes

Loading…