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

HRID 83877Notes

Reaction equation

HRID 83877 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([Br:14])[CH:8]=1)(=O)=O.[C-:15]#[N:16].[Na+]>CN(C=O)C>[Br:14][C:9]1[CH:8]=[C:7]([CH2:6][C:15]#[N:16])[CH:12]=[CH:11][C:10]=1[F:13]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 598548133-Bromo-4-fluorobenzyl methanesulfonate

Product 1

HCID 201138972-(3-Bromo-4-fluorophenyl)acetonitrileYield 66.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-bromo-4-fluorobenzyl methanesulfonate (60 g, 0.212 mol) in DMF (300 mL) at 0° C. was added NaCN (31.1 g, 0.635 mol, 3 eq) portionwise. After stirring at room temperature 4 h, the reaction mixture was partitioned in EtOAc and water. The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography (Hex/EtOAc=4:1) to give 2-(3-bromo-4-fluorophenyl)acetonitrile (30 g, 3 step overall yield: 55%). 1H NMR (400 MHz, CDCl3) δ 7.56-7.54 (m, 1H), 7.28-7.24 (m, 1H), 7.14 (t, J=4.4 Hz, 1H), 3.73 (s, 2H).

Workup

  1. customthe reaction mixture was partitioned in EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography (Hex/EtOAc=4:1)

Sources & evidence

ORD record
ord-28c057370e8b4757ad56f0f460479e00
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

Loading…