2-Fluoro-6-methoxybenzonitrile → 2-Fluoro-6-hydroxybenzonitrile

HRID 1635687Notes

Reaction equation

HRID 1635687 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:4]=1[C:5]#[N:6].Cl.N1C=CC=CC=1>>[F:11][C:7]1[C:4]([C:5]#[N:6])=[C:3]([OH:2])[CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 5231012-Fluoro-6-methoxybenzonitrileHCID 10176127Pyridinium chloride

Product 1

HCID 27832162-Fluoro-6-hydroxybenzonitrileYield 66.4%

Procedure

7.8 g of 2-methoxy-6-fluorobenzonitrile and 18.0 g of pyridine hydrochloride were heated for 5 hours at 195° C. under dry nitrogen. After cooling, the batch was partitioned between 50 ml of water and 50 ml of tert-butyl methyl ether, and the organic phase was subsequently extracted with 40 ml of 2N NaOH. The alkali extract was brought to pH 5 and subsequently extracted twice with in each case 40 ml of tert-butyl methyl ether. After the solvent had been evaporated, 4.7 g of the desired product were obtained as an oil (HPLC: 93%).

Workup

  1. temperatureAfter cooling
  2. customthe batch was partitioned between 50 ml of water and 50 ml of tert-butyl methyl ether
  3. extractionthe organic phase was subsequently extracted with 40 ml of 2N NaOH
  4. extractionThe alkali extract
  5. extractionsubsequently extracted twice with in each case 40 ml of tert-butyl methyl ether
  6. customAfter the solvent had been evaporated

Sources & evidence

ORD record
ord-d6223bb1ed394681b8402df553b6ff67
Source dataset
uspto-grants-2003_01
Patent number
US06509501B2

Reaction notes

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