Acetic Anhydride → 2-(2,4-Dichloro-5-fluorobenzoyl)3-methoxy-acrylonitrile

HRID 981346Notes

Reaction equation

HRID 981346 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([F:14])=[CH:9][C:3]=1[C:4]([CH2:6][C:7]#[N:8])=[O:5].[C:15]([O:18][C:19](=O)C)(=O)C>>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([F:14])=[CH:9][C:3]=1[C:4]([C:6](=[CH:15][O:18][CH3:19])[C:7]#[N:8])=[O:5]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 136307213-(2,4-Dichloro-5-fluorophenyl)-3-oxopropanenitrile

Product 1

HCID 537325472-(2,4-Dichloro-5-fluorobenzoyl)3-methoxy-acrylonitrileYield 99%

Conditions

Temperature
150 °C

Procedure

A mixture of 21 g of 2,4-dichloro-5-fluoro-benzoyl-acetonitrile, 19.2 g of methyl o-formate and 23.1 g of acetic anhydride is refluxed at a bath temperature of 150° C. for 3 hours. The volatile constituents are then distilled off under a waterpump vacuum and finally under a fine vacuum at a bath temperature of 120° C. 24.5 g (99%) of 2-(2,4-dichloro-5-fluorobenzoyl)3-methoxy-acrylonitrile are obtained. A sample recrystallized from toluene gives colorless crystals of melting point 159° C.

Workup

  1. distillationThe volatile constituents are then distilled off under a waterpump vacuum and finally under a fine vacuum at a bath temperature of 120° C

Sources & evidence

ORD record
ord-08a6575a81fd4d8ab6506bbcd1589d3a
Source dataset
uspto-grants-1991_02
Patent number
US04990646

Reaction notes

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