Thionyl Chloride → HCID 86683152, compound

HRID 920938Notes

Reaction equation

HRID 920938 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)[O:5][CH:6]=1.S(Cl)([Cl:14])=O>ClC(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4](/[CH:7]=[CH:8]/[C:9]([Cl:14])=[O:11])[O:5][CH:6]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 83764663HCID 83764663, compound

Product 1

HCID 86683152HCID 86683152, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-(4-bromofuran-2-yl)acrylic acid (3.8 g, 17.51 mmol) in 35 mL of trichloromethane was added a solution of 2.6 mL of thionyl chloride in 200 μL of DMF. The reaction mixture was refluxed for 1 h and after cooling to room temperature concentrated to give 4 g (97% yield) of the title compound as light brown oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-11e0addf4940428392a0cc9bd0cf2d9c
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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