Dimethylformamide → 4-(fluoromethyl)benzoyl Chloride

HRID 857232Notes

Reaction equation

HRID 857232 reaction equation
[F:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.CN(C)C=O.S(Cl)([Cl:19])=O>C1C=CC=CC=1>[F:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:19])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 139813684-(Fluoromethyl)benzoic acid

Product 1

HCID 218666964-(fluoromethyl)benzoyl Chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
40 °C

Procedure

4-(Fluoromethyl)benzoic acid (6.20 g) was dissolved in 30 ml of benzene, and 0.3 ml of N,N-dimethylformamide was added and then 4.4 ml of thionyl chloride was added dropwise. The mixture was stirred for 1 hour at 40° C. and then heated to reflux for another 1 hour. The solvent was distilled off under reduced pressure to provide 6.70 g of the objective compound as pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for another 1 hour
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b57ceada4d14427da98843fdfed223e8
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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