Dimethylformamide → 4-Fluoro-2-hydroxybenzoyl chloride

HRID 457951Notes

Reaction equation

HRID 457951 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([OH:11])[CH:3]=1.S(Cl)([Cl:14])=O.CN(C)C=O>CCCCCCC>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:14])=[O:7])=[C:4]([OH:11])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 676614-Fluorosalicylic acid

Product 1

HCID 184681274-Fluoro-2-hydroxybenzoyl chlorideYield 85%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 4-fluoro-2-hydroxy-benzoic acid (15 g, 96.1 mmol) in heptane (190 mL) was treated with thionyl chloride (21 mL, 288 mmol) in a dropwise manner over 30 min. A drop of N,N-dimethylformamide was added and the solution was heated for 4 h at 60° C. The excess thionyl chloride was distilled off under reduced pressure. The remaining solution was cooled to room temperature, filtered, and concentrated to give 4-fluoro-2-hydroxy-benzoyl chloride as a pale yellow crystalline solid (14.2 g, 85%).

Workup

  1. distillationThe excess thionyl chloride was distilled off under reduced pressure
  2. temperatureThe remaining solution was cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-65d1a24e22fa4cf4aa42121ab83e7d40
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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