Acetic Anhydride → 3-Cyano-2-fluoro-6-methoxyphenyl acetate

HRID 2260263Notes

Reaction equation

HRID 2260263 reaction equation
[F:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:10][C:9]1[C:8]([O:11][CH3:12])=[CH:7][CH:6]=[C:3]([C:4]#[N:5])[C:2]=1[F:1])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 214591072-Fluoro-3-hydroxy-4-methoxybenzonitrile

Product 1

HCID 539089783-Cyano-2-fluoro-6-methoxyphenyl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.9 g of 2-fluoro-3-hydroxy-p-anisonitrile are dissolved in 10 ml of acetic anhydride and 0.5 ml of pyridine, whereupon the mixture is stirred at 120° for 2 hours. The reaction mixture is subsequently evaporated and the residue is partitioned between ice-water and methylene chloride. The organic phase is dried over sodium sulfate and evaporated, and the residue is recrystallized from methylene chloride/hexane. There is obtained 3-cyano-2-fluoro-6-methoxyphenyl acetate of m.p. 90°-91°.

Workup

  1. customThe reaction mixture is subsequently evaporated
  2. customthe residue is partitioned between ice-water and methylene chloride
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customthe residue is recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-b384deb61f8d46feaf459ba6e4db8710
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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