Thionyl Chloride → 2-Fluoro-5-methylbenzoyl chloride

HRID 2414378Notes

Reaction equation

HRID 2414378 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:14])=O>>[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2428292-Fluoro-5-methylbenzoic acid

Product 1

HCID 70180482-Fluoro-5-methylbenzoyl chloride

Procedure

A mixture of 2-fluoro-5-methylbenzoic acid (41.05 g, 0.266 mol) in thionyl chloride (200 mL) is refluxed for 45 min., during which time it becomes homogeneous. After cooling, the thionyl chloride is evaporated to yield 2-fluoro-5-methylbenzoyl chloride, as a yellow liquid, which is dissolved in CH2Cl2 (500 mL), and cooled to 0° C. To this solution is added 2-(trimethylsilyl)-ethanol (48.65 mL, 40.14 g, 0.34 mol), followed by triethylamine (85.86 g, 118.3 mL, 0.85 mol), and the solution is warmed to room temp. over 1 h. The solution is then washed with 1 N HCl (2×500 mL), water (1×250 mL) and brine (1×100 mL), dried (MgSO4), evaporated and chromatographed (silica, 5% EtOAc/hexane) to yield (2-trimethylsilyl)-ethyl 2-fluoro-5-methylbenzoate, as a yellow oil.

Workup

  1. temperatureis refluxed for 45 min., during which time it
  2. temperatureAfter cooling
  3. customthe thionyl chloride is evaporated

Sources & evidence

ORD record
ord-3fa5f02955324033920d804052ccd055
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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