Sodium Cyanide → 2-(4-Bromo-3-fluorophenyl)acetonitrile

HRID 1850037Notes

Reaction equation

HRID 1850037 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Br:10])[CH2:5]Br.[C-:11]#[N:12].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][C:11]#[N:12])[CH:7]=[CH:8][C:9]=1[Br:10]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 116661761-Bromo-4-(bromomethyl)-2-fluorobenzene

Product 1

HCID 116009532-(4-Bromo-3-fluorophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

This crude benzyl bromide (27 mmol) and sodium cyanide (2.38 g, 54 mmol, 2.0 eq.) were combined in ethanol (100 mL) and heated at 80° C. for 2 h. The reaction mixture was concentrated to dryness in vacuo, suspended in water, and extracted with ethyl acetate. Washing with brine and drying over Na2SO4 gave, after removal of the solvent, a red oil which was purified using silica gel chromatography (gradient of 2→12% ethyl acetate/hexanes) to provide 3-fluoro-4-bromophenylacetonitrile as white needles (1.96 g, 35% over 2 steps).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness in vacuo
  2. extractionextracted with ethyl acetate
  3. washWashing with brine
  4. dry with materialdrying over Na2SO4
  5. customgave
  6. customafter removal of the solvent
  7. customa red oil which was purified

Sources & evidence

ORD record
ord-54ac1a7c9d204d80a210986190240fa0
Source dataset
uspto-grants-2015_02
Patent number
US08957049B2

Reaction notes

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