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

HRID 395021Notes

Reaction equation

HRID 395021 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-7757f12728514c00b9cf1852b6cd9d50
Source dataset
uspto-grants-2003_08
Patent number
US06603019B2

Reaction notes

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