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

HRID 425328Notes

Reaction equation

HRID 425328 reaction equation
[C-:1]#[N:2].[Na+].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]Br)=[CH:7][C:6]=1[F:13]>O.C(O)C>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:1]#[N:2])=[CH:7][C:6]=1[F:13]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Powered sodium cyanide (12.0 g, 0.24 mol) was dissolved in a 20 mL of water, and was added a solution of 1-bromo-4-(bromomethyl)-2-fluorobenzene (60 g, 0.22 mol) in 30 mL of ethanol. After heating at reflux for 4 h, the reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the residue was diluted with CH2Cl2, filtered, and concentrated to afford (4-bromo-3-fluorophenyl)acetonitrile, which was used without further purification.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 4 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. additionthe residue was diluted with CH2Cl2
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-69abb13e9dac4726a5adc95417f71432
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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