Dimethylformamide → 2-(3,5-Difluorophenyl)acetyl chloride

HRID 2180167Notes

Reaction equation

HRID 2180167 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.C(Cl)(C([Cl:17])=O)=O.CN(C=O)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([Cl:17])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1454243,5-Difluorophenylacetic acid

Product 1

HCID 27827232-(3,5-Difluorophenyl)acetyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3,5-difluorophenyl acetic acid (0,172 g, 1 mmol) in CH2Cl2 (1 mL) at room temperature under Ar was added (COCl)2 (0.175 mL, 2 mmol, 2 eq.) followed by DMF (0.01 mL, catalyst). The resulting mixture was stirred at room temperature for 16 h. The mixture was concentrated by rotary evaporation and the resulting oil was evaporated from CH2Cl2 (2×5 mL) and toluene (1×5 mL) and dried under high vacuum for 1 h to give (3,5-difluoro-phenyl)-acetyl chloride as a pale yellow oil.

Workup

  1. concentrationThe mixture was concentrated by rotary evaporation
  2. customthe resulting oil was evaporated from CH2Cl2 (2×5 mL) and toluene (1×5 mL)
  3. customdried under high vacuum for 1 h

Sources & evidence

ORD record
ord-c8207762ad2a447b83cafa0fd009ca27
Source dataset
uspto-grants-2005_05
Patent number
US06887889B2

Reaction notes

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