Thionyl Chloride → 2-Fluoro-5-methoxybenzoyl chloride

HRID 1761017Notes

Reaction equation

HRID 1761017 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:15])=O>CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27745432-Fluoro-5-methoxybenzoic acid

Product 1

HCID 225942222-Fluoro-5-methoxybenzoyl chlorideYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 2-fluoro-5-methoxy-benzoic acid (4.3 g, 25 mmol) and thionyl chloride (68 mL, 937 mmol) and DMF (1 drop) was stirred at RT for 14 hours. The mixture was then evaporated to afford the title compound (4.77 g, 100%) after repeated azeotroping with toluene.

Workup

  1. customThe mixture was then evaporated

Sources & evidence

ORD record
ord-c6f3de25f5534314ab8f0505879369dd
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

Loading…