Thionyl Chloride → 3-(3-Bromo-4-fluoro-phenyl)-acryloyl chloride

HRID 2207879Notes

Reaction equation

HRID 2207879 reaction equation
[Br: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>>[Br: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

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 6883113-(3-Bromo-4-fluorophenyl)-2-propenoic acid

Product 1

HCID 27569963-(3-Bromo-4-fluoro-phenyl)-acryloyl chloride

Conditions

Temperature
100 °C

Procedure

3-(3-Bromo-4-fluoro-phenyl)-acrylic acid (3.3 g, 13.3 mmol) prepared in Step 1 was added to thionyl chloride (10.0 mL). The reaction mixture was stirred at 100° C. for 2 hours, concentrated under reduced pressure. The resulting residue was concentrated under reduced pressure three times, along with using toluene, to give 3.5 g of the titled compound as an unpurified dark brown liquid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationThe resulting residue was concentrated under reduced pressure three times, along with using toluene

Sources & evidence

ORD record
ord-1bc6024e22d84855b8396c2585ada29d
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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