Water → 4-Fluoro-2-hydroxybenzonitrile

HRID 2233301Notes

Reaction equation

HRID 2233301 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10]C)[CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].O>ClC(Cl)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:10])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27833294-Fluoro-2-methoxybenzonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 110299014-Fluoro-2-hydroxybenzonitrileYield 86%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1 g of 4-fluoro-2-methoxy-benzonitrile in 15 mL of dichloroethane was added 1.1 g of aluminum trichloride. The resulting mixture was refluxed for 1 day then poured slowly into water and extracted with ethyl acetate. The organic extracts were washed twice with 10% aqueous solution of sodium hydroxide. The combined basic layers were washed twice with ethyl acetate, acidified with concentrated aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic extracts were washed with water, with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 0.78 g of 4-fluoro-2-hydroxy-benzonitrile as a white solid.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 day
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed twice with 10% aqueous solution of sodium hydroxide
  4. washThe combined basic layers were washed twice with ethyl acetate
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic extracts were washed with water, with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b935a99d47ff4694b9e5896d29a1434c
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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