Water → 2-Fluoro-4-(hydroxymethyl)benzonitrile

HRID 413414Notes

Reaction equation

HRID 413414 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[F:10].O.[CH3:12][N:13](C=O)C>[C-]#N.[Zn+2].[C-]#N>[F:10][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:8]=[CH:9][C:2]=1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 20682297(4-Bromo-3-fluorophenyl)methanol

Product 1

HCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
95 °C

Procedure

4-Bromo-3-fluorobenzyl alcohol (20 g, 0.097 mol) was dissolved in DMF (100 mL) then placed under high vacuum for 15 min. The solution was then purged with Ar for 15 min. While purging continued, zinc cyanide (8 g, 0.068 mol) and the catalyst, Pd[(PPh3)]4, (5.63 g, 0.0049 mol) were added. The reaction mixture was heated at 95° C. under Ar for 18 h, then cooled to ambient temperature and added to H2O. The mixture was extracted with EtOAc, then washed with 1M HCl, H2O, brine, and dried (Na2SO4). Filtration and concentration to dryness gave the title compound as a white solid after chromatography (silica gel, hexane: EtOAc, 6.5:3.5).

Workup

  1. customThe solution was then purged with Ar for 15 min
  2. customWhile purging
  3. temperaturecooled to ambient temperature
  4. extractionThe mixture was extracted with EtOAc
  5. washwashed with 1M HCl, H2O, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-0376db198f4a4c5a80afd398e4b4079c
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

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