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

HRID 1859160Notes

Reaction equation

HRID 1859160 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.CN(C=O)C.C(Cl)(=O)C([Cl:21])=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([Cl:21])=[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

Conditions

Temperature
0 °C

Procedure

3,5-Difluorophenylacetic acid (30 g, 0.174 mol) (Aldrich) was dissolved in dichloromethane and this solution was cooled to 0° C. DMF (0.5 mL, catalytic) was added followed by the dropwise addition of oxalyl chloride (18 mL, 0.20 mol) over a 5 minute period. The reaction was stirred for 3 h and then rotoevaporated at reduced pressure to a residue which was placed on a high vacuum pump for 1 h to afford 3,5-difluorophenylacetyl chloride as a thin yellow oil. Other acid chlorides can be prepared in a similar manner.

Workup

  1. waitwas placed on a high vacuum pump for 1 h

Sources & evidence

ORD record
ord-fba3c4efa1f541d681434d2574572036
Source dataset
uspto-grants-2000_11
Patent number
US06153652

Reaction notes

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