Dimethylformamide → 4-Fluorophenylacetyl chloride

HRID 2213341Notes

Reaction equation

HRID 2213341 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.CN(C=O)C>C(Cl)Cl>[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 3

HCID 6228DimethylformamideHCID 98372-(4-Fluorophenyl)acetic acidHCID 65578Oxalyl chloride

Product 1

HCID 37449884-Fluorophenylacetyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-fluorophenylacetic acid (12.2 g, 79 mmol.) in dry DCM (200 ml) at 0° C. was added oxalyl chloride (7.8 ml, 89 mmol.) and DMF (0.3 ml) and the resulting effervescing mixture stirred at 0° C. for 30 minutes then at ambient temperature for a further 45 minutes. 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 4-fluorophenylacetyl chloride.

Workup

  1. waitat ambient temperature for a further 45 minutes
  2. customthe solvent was evaporated
  3. additionTo the residue was added toluene (50 ml)
  4. customthe solvent evaporated
  5. additionThe addition of toluene and evaporation

Sources & evidence

ORD record
ord-4fb21042aaec4608a4b651897b4e5b69
Source dataset
uspto-grants-2006_09
Patent number
US07105509B2

Reaction notes

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