2-(4-Fluorophenyl)acetic acid → 4-Fluorophenylacetyl chloride

HRID 2213342Notes

Reaction equation

HRID 2213342 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.C(Cl)(=O)C([Cl:15])=O>C1COCC1.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([Cl:15])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 98372-(4-Fluorophenyl)acetic acidHCID 65578Oxalyl chloride

Product 1

HCID 37449884-Fluorophenylacetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-fluorophenylacetic acid (11.2 g, 73 mmol.) in THF (125 ml) at 0° C. under nitrogen was added oxalyl chloride (7.1 ml, 82 mmol.) then DMF (4 drops) and the resulting effervescing mixture stirred at 0° C. for 30 minutes then at ambient temperature for a further 1 hour. The effervescence had ceased after this time and the solvent was evaporated. To the residue was added toluene (50 ml) and the solvent evaporated. The addition of toluene and evaporation was repeated to leave a residue of 4fluorophenylacetyl chloride.

Workup

  1. customthe solvent was evaporated
  2. additionTo the residue was added toluene (50 ml)
  3. customthe solvent evaporated
  4. additionThe addition of toluene and evaporation

Sources & evidence

ORD record
ord-6c0769c0a73340a88fe5e11ee55970b5
Source dataset
uspto-grants-2006_09
Patent number
US07105509B2

Reaction notes

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