Acetic Anhydride → HCID 53655523, compound

HRID 1788976Notes

Reaction equation

HRID 1788976 reaction equation
[F:1][C:2]1[C:12]([F:13])=[C:11]([F:14])[C:10]([F:15])=[CH:9][C:3]=1[C:4]([CH2:6][C:7]#[N:8])=[O:5].[CH:16]([O-])([O-])[O:17][CH2:18][CH3:19].C(OC(=O)C)(=O)C>>[CH2:18]([O:17][CH:16]=[C:6]([C:4](=[O:5])[C:3]1[CH:9]=[C:10]([F:15])[C:11]([F:14])=[C:12]([F:13])[C:2]=1[F:1])[C:7]#[N:8])[CH3:19]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 139117863-Oxo-3-(2,3,4,5-tetrafluorophenyl)propanenitrileHCID 53630039Ethylorthoformate

Product 1

HCID 53655523HCID 53655523, compoundYield 88%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(2,3,4,5-tetrafluorobenzoyl)acetonitrile (13.1 g), ethyl orthoformate (13.4 g) and acetic anhydride (15.4 g) is heated at 100° C. with stirring for 3 hours. The reaction mixture is concentrated under vacuum to yield an orange brownish oily residue. When the oily residue is allowed to stand at room temperature, it crystallizes slowly. The resulting crystals are collected and washed successively with a 2:1 mixture of hexane and ethyl acetate, and a 5:1 mixture of hexane and ethyl acetate to give 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrile (14.5 g) as light orange crystals, m.p. 99°-101° C.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. customto yield an orange brownish oily residue
  3. customto stand at room temperature
  4. customit crystallizes slowly
  5. customThe resulting crystals are collected
  6. washwashed successively with a 2:1 mixture of hexane and ethyl acetate
  7. additiona 5:1 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-f4e9bacf1cdc4752baaef28e79f8c8f7
Source dataset
uspto-grants-1987_08
Patent number
US04686221

Reaction notes

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