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

HRID 1627362Notes

Reaction equation

HRID 1627362 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-086fcc8ebe6c42378a726f37196031fe
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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