Dimethylformamide → 3-(3,4-Difluorophenyl)prop-2-enoyl chloride

HRID 1773443Notes

Reaction equation

HRID 1773443 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[F:7][C:8]1[CH:9]=[C:10](/[CH:15]=C/C(O)=O)[CH:11]=[CH:12][C:13]=1[F:14].CN(C)C=O>ClCCl>[F:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:1][C:2]([Cl:4])=[O:3])[CH:11]=[CH:12][C:13]=1[F:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2733300trans-3,4-Difluorocinnamic acid

Product 1

HCID 713606863-(3,4-Difluorophenyl)prop-2-enoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0-5° C., oxalyl dichloride (25.7 g, 202.36 mmol, 3.00 equiv.) was added to a mixture of (E)-3-(3,4-difluorophenyl)acrylic acid (12.4 g, 67.38 mmol, 1.00 equiv.), N,N-dimethylformamide (1 mL), and dichloromethane (150 mL). The solution was stirred at ambient temperature for about 2 hours, and then concentrated in vacuo to give the title product, which was used in the next step without any further purification.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-147ebcd1697c4e95a71ca69f96a2664d
Source dataset
uspto-grants-2016_02
Patent number
US09255104B2

Reaction notes

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