2-Fluoro-4-methoxybenzonitrile → 2-Fluoro-4-hydroxybenzonitrile

HRID 2209741Notes

Reaction equation

HRID 2209741 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10]C)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.N1C=CC=CC=1>>[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 6398782-Fluoro-4-methoxybenzonitrileHCID 10176127Pyridinium chloride

Product 1

HCID 27346752-Fluoro-4-hydroxybenzonitrile

Conditions

Temperature
170 °C

Procedure

A mixture of 2-fluoro-4-methoxy-benzonitrile (500 mg, 0.246 mmol) and pyridine hydrochloride (2.0 g, 17.2 mmol) is heated at 170° C. for 5 hours. The reaction is partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase is washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 2-fluoro-4-hydroxy-benzonitrile.

Workup

  1. customThe reaction is partitioned between ethyl acetate and 1N hydrochloric acid
  2. washThe organic phase is washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a96a04da4d1749ff97d54f991672cc43
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

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