Dimethylformamide → 4-Fluorophenylacetyl chloride

HRID 1977786Notes

Reaction equation

HRID 1977786 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.CN(C)C=O.S(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([Cl:19])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 98372-(4-Fluorophenyl)acetic acidHCID 24386Thionyl Chloride2×

Product 1

HCID 37449884-Fluorophenylacetyl chlorideYield 89.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 150 g (0.974 mol) of 4-fluorophenylacetic acid an 1 mL of N,N-dimethylformamide in 500 mL of toluene at 40° C. was treated with 20 mL of thionyl chloride and heated to 40° C. An additional 61.2 mL of thionyl chloride was added dropwise over 1.5 hours. After the addition, the solution was heated at 50° C. for 1 hour, the solvent was removed in vacuo and the residual oil was distilled at reduced pressure (1.5 mmHg) to afford 150.4 g (89.5%) of the title compound, bp=68-70° C.

Workup

  1. additionAfter the addition
  2. temperaturethe solution was heated at 50° C. for 1 hour
  3. customthe solvent was removed in vacuo
  4. distillationthe residual oil was distilled at reduced pressure (1.5 mmHg)

Sources & evidence

ORD record
ord-35c31972d4db464b9a6c1be39b099389
Source dataset
uspto-grants-2001_05
Patent number
US06235735B1

Reaction notes

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