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

HRID 2229883Notes

Reaction equation

HRID 2229883 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-ff5137332a87472cbae311858b2d2dfa
Source dataset
uspto-grants-2002_07
Patent number
US06420605B1

Reaction notes

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