Thionyl Chloride → 5-Fluoro-2-methylbenzoyl chloride

HRID 1037833Notes

Reaction equation

HRID 1037833 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].S(Cl)([Cl:14])=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([Cl:14])=[O:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 1821145-Fluoro-2-methylbenzoic acid

Product 1

HCID 27373835-Fluoro-2-methylbenzoyl chloride

Procedure

A solution of 5-fluoro-2-methylbenzoic acid (380 mg, 2.47 mmol) in thionyl chloride (5 mL) was heated to reflux for 3 hours. The solution was cooled to ambient temperature and the volatile components were removed under reduced pressure. The residue was dissolved in fresh toluene (10 mL) and concentrated under reduced pressure twice and then placed under high vacuum to afford the title compound (420 mg).

Workup

  1. temperatureto reflux for 3 hours
  2. customthe volatile components were removed under reduced pressure
  3. dissolutionThe residue was dissolved in fresh toluene (10 mL)
  4. concentrationconcentrated under reduced pressure twice

Sources & evidence

ORD record
ord-4c02775a537c494b884c2fced5ee7d1d
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

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