Thionyl Chloride → (2E)-3-(3,4-Difluorophenyl)-2-propenoyl chloride

HRID 130589Notes

Reaction equation

HRID 130589 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[F:8].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([Cl:16])=[O:13])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 2733300trans-3,4-Difluorocinnamic acid

Product 1

HCID 9920680(2E)-3-(3,4-Difluorophenyl)-2-propenoyl chlorideYield 99.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
65 °C

Procedure

A stirred mixture of (E)-3-(3,4-difluorophenyl)-2-propenoic acid (8.2 kg), toluene (7.4 kg) and pyridine (0.18 kg) was heated to 65° C. and then thionyl chloride (7.4 kg) was added over 30 minutes. The reaction was stirred for a further 2 h 15 minutes after the addition was complete, then diluted with toluene (8.7 kg). Excess thionyl chloride, sulfur dioxide and hydrogen chloride were then distilled out, together with toluene (10 L), under reduced pressure, yielding a solution of the (E)-3-(3,4-difluorophenyl)-2-propenoyl chloride (approximately 9 kg) in toluene.

Workup

  1. additionafter the addition
  2. distillationExcess thionyl chloride, sulfur dioxide and hydrogen chloride were then distilled out, together with toluene (10 L), under reduced pressure

Sources & evidence

ORD record
ord-b2e396f982044756a4716503150d9634
Source dataset
uspto-grants-2008_06
Patent number
US07381828B2

Reaction notes

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