Thionyl Chloride → 3-(5-Bromo-pyridin-3-yl)-acryloyl chloride

HRID 2207893Notes

Reaction equation

HRID 2207893 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]([OH:12])=O)[CH:5]=[N:6][CH:7]=1.S(Cl)([Cl:15])=O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]([Cl:15])=[O:12])[CH:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27847353-(5-Bromopyridin-3-yl)prop-2-enoic acid

Product 1

HCID 1317359453-(5-Bromo-pyridin-3-yl)-acryloyl chloride

Conditions

Temperature
100 °C

Procedure

3-(5-Bromo-pyridin-3-yl)-acrylic acid (26.2 g, 114.7 mmol) prepared in Step 1 was added to thionyl chloride (100.0 mL). The reaction mixture was stirred at 100° C. for 2 hours and then concentrated under reduced pressure. The resulting residue was concentrated under reduced pressure three times, along with using toluene, to give 3-(5-bromo-pyridin-3-yl)-acryloyl chloride 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-01fe754c286948e4b62d352405604faf
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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