Dimethylformamide → 4-Fluoro-3-nitrobenzoyl chloride

HRID 966143Notes

Reaction equation

HRID 966143 reaction equation
[F: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].CN(C)C=O.C(Cl)(=O)C([Cl:22])=O>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:22])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 27833474-Fluoro-3-nitrobenzoyl chlorideYield 106.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-3-nitrobenzoic acid (20 g, 0.108 mol) in dichloromethane (0.5 L) were added dimethyl formamide (0.1 mL) and oxalyl chloride (47 mL, 0.54 mol) over 20 min. After 1 h, the mixture was concentrated in vacuo to afford the acid chloride, 4-fluoro-3-nitro-benzoyl chloride (23.32 g) as yellow oil which was used without further purification.

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-3719a007a6a3441a834754564798c7d1
Source dataset
uspto-grants-2005_10
Patent number
US06951859B2

Reaction notes

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