Water → 2-(2-Fluoro-4-iodophenyl)acetonitrile

HRID 2299323Notes

Reaction equation

HRID 2299323 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Br.O.[C-:12]#[N:13].[Na+]>C(O)C>[F:1][C:2]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:3]=1[CH2:4][C:12]#[N:13]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 222404061-(Bromomethyl)-2-fluoro-4-iodobenzene2×

Product 1

HCID 222405322-(2-Fluoro-4-iodophenyl)acetonitrileYield 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-fluoro-4-iodo-benzyl bromide (Intermediate 1, 2.56 g, 8.15 mmol) in ethanol (55 mL and water (10 mL) was treated with sodium cyanide (2.15 g, 43.86 mmol) and refluxed for 0.5 h. The volatiles were distilled off in vacuo and the residue was diluted with water and extracted with diethyl ether (×2). The combined organic extract was washed with water (×1) and brine (×1), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound as a pale yellow solid (2.05 g, 96%).

Workup

  1. temperaturerefluxed for 0.5 h
  2. distillationThe volatiles were distilled off in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with diethyl ether (×2)
  5. extractionThe combined organic extract
  6. washwas washed with water (×1) and brine (×1)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-8d16308fc99f46b69ae0e3e2de0c2b08
Source dataset
uspto-grants-2002_12
Patent number
US06495552B2

Reaction notes

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