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

HRID 1700170Notes

Reaction equation

HRID 1700170 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), prepared as described in Step B, 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-e8dfeb221c114218938506a36f4b0944
Source dataset
uspto-grants-2002_02
Patent number
US06350755B1

Reaction notes

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