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

HRID 7704

Reaction equation

HRID 7704 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[C:4]([F:10])[CH:3]=1.[C-:11]#[N:12].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:11]#[N:12])=[C:4]([F:10])[CH:3]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 4-bromo-2-fluoro benzyl bromide (1.5 g, 5.6 mmol) in DMF (50 mL) was added sodium cyanide (0.8 g, 16.8 mmol). The reaction was stirred at 90° C. for 1 h, and cooled at rt. After quenching with brine (50 mL) and diluted with EtOAc (100 mL), the EtOAc layer was washed with brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, hexanes:EtOAc 5:1) to afford 4-bromo-2-fluoro benzyl cyanide as yellow solid. MS (ESI) 307 (M+H)+.

Workup

  1. temperaturecooled at rt
  2. customAfter quenching with brine (50 mL)
  3. additiondiluted with EtOAc (100 mL)
  4. washthe EtOAc layer was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (silica gel, hexanes:EtOAc 5:1)

Sources & evidence

ORD record
ord-57e9aff840d84b2daacf95eb7f45676b
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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