p-Bromocinnamic acid → 3-(4-Bromophenyl)prop-2-enoyl chloride

HRID 2289798Notes

Reaction equation

HRID 2289798 reaction equation
BrC1C=C2C(C(Cl)=CN=C2[Cl:12])=CC=1.[Br:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]=[CH:20][C:21](O)=[O:22])=[CH:17][CH:16]=1>O=S(Cl)Cl>[Br:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]=[CH:20][C:21]([Cl:12])=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 99777p-Bromocinnamic acidHCID 166583507-Bromo-1,4-dichloroisoquinoline

Product 1

HCID 534112933-(4-Bromophenyl)prop-2-enoyl chloride

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

7-Bromo-1,4-dichloroisoquinoline ##STR100## A solution of 4-bromocinnamic acid (5.03 g, 22.2 mmol) in SOCl2 (15 mL) was stirred at 23° C. for 16 h, and then heated at reflux for a further 2 h. The solvents were evaporated in vacuo and the residue azeotroped with PhMe (×3) to yield 4-bromocinnamoyl chloride (22 mmol) as an orange-brown solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for a further 2 h
  3. customThe solvents were evaporated in vacuo
  4. customthe residue azeotroped with PhMe (×3)

Sources & evidence

ORD record
ord-8fd47bf109574ab49119dd7afc3a2cdc
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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