Dimethylformamide → 2-(2-Fluorophenyl)acetyl chloride

HRID 1638162Notes

Reaction equation

HRID 1638162 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.CN(C)C=O.S(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([Cl:19])=[O:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 67979Benzeneacetic acid, 2-fluoro-

Product 1

HCID 140040112-(2-Fluorophenyl)acetyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
22.5 °C

Procedure

A solution of 50.0 g of o-fluorophenylacetic acid in 150 mL of toluene and 2.2 g of N,N-dimethylformamide is added to 50.2 g (31.7 mL) of thionyl chloride with efficient stirring over a period of 20 minutes while maintaining an internal temperature of 20-25° C. After addition, the mixture is stirred for 3 hours at 20-25° C., and concentrated to dryness under reduced pressure (66-76 mm Hg, bath temperature 65-70° C.) to obtain 2-fluorobenzenacetyl chloride as an oil.

Workup

  1. additionAfter addition
  2. stirringthe mixture is stirred for 3 hours at 20-25° C.
  3. concentrationconcentrated to dryness under reduced pressure (66-76 mm Hg, bath temperature 65-70° C.)

Sources & evidence

ORD record
ord-678a46d0657846acb5f05407502267d7
Source dataset
uspto-grants-2000_03
Patent number
US06043365

Reaction notes

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