Oxalyl chloride → 3-{4-[(4-Fluorophenyl)methoxy]phenyl}prop-2-enoyl chloride

HRID 724750Notes

Reaction equation

HRID 724750 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:18]=[CH:17][C:11]([CH:12]=[CH:13][C:14]([O-])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:24])=O>>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:18]=[CH:17][C:11]([CH:12]=[CH:13][C:14]([Cl:24])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 65578Oxalyl chlorideHCID 53456323HCID 53456323, compound

Product 1

HCID 541626113-{4-[(4-Fluorophenyl)methoxy]phenyl}prop-2-enoyl chloride

Procedure

7.34 g (0.027 mol) of 4-(4-fluorobenzyloxy)cinnamate and 15.0 ml of oxalyl chloride were placed in a 100 ml flask that was provided with a cooling tube, and allowed to react for 4 hours at 70° C. The excess oxalyl chloride was removed under reduced pressure, to obtain 4-(4-fluorobenzyloxy)cinnamoyl chloride. After confirming the compound's structure with IR and NMR, it was immediately used in the following reaction.

Workup

  1. customthat was provided with a cooling tube
  2. customto react for 4 hours at 70° C
  3. customThe excess oxalyl chloride was removed under reduced pressure

Sources & evidence

ORD record
ord-10d652d97e4a4f0e98620ea0c3c85af2
Source dataset
uspto-grants-1998_01
Patent number
US05705096

Reaction notes

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