Water → 2-(4-Bromo-2-fluorophenyl)acetonitrile

HRID 533517Notes

Reaction equation

HRID 533517 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[CH2:9]Cl.[C-:11]#[N:12].[Na+].O>CN(C=O)C>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][C:11]#[N:12])=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 27733614-Bromo-1-(chloromethyl)-2-fluorobenzene

Product 1

HCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrileYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-4-bromo-chloromethylbenzene (25.0 g, 112 mmol) and NaCN (6.32 g, 129 mmol) were dissolved in DMF (70 mL) and the solution was stirred under a N2 atmosphere for 18 hrs at ambient temperature. The solution was poured into water (300 mL), and was extracted with EtOAc (1×1 L, 4×300 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure, yielding the title compound (22.5 g, 105 mmol, 93%) as a yellow oil that contained some traces of DMF. 1H-NMR (CDCl3, 300 MHz): 3.75 (s, 2H); 7.20-7.4 (m, 3H)

Workup

  1. extractionwas extracted with EtOAc (1×1 L, 4×300 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e2b3aa2aee34c4fba274abf193b1913
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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