Sodium Cyanide → 2-(4-Bromo-2,3-difluorophenyl)acetonitrile

HRID 1050035Notes

Reaction equation

HRID 1050035 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([F:10])[C:3]=1[F:11].[C-:12]#[N:13].[Na+]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:12]#[N:13])=[C:4]([F:10])[C:3]=1[F:11]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 696728541-Bromo-4-(bromomethyl)-2,3-difluorobenzene

Product 1

HCID 904160312-(4-Bromo-2,3-difluorophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 1-bromo-4-(bromomethyl)-2,3-difluorobenzene (330 mg, 1.154 mmol) in EtOH (10 mL) stirred under N2 at 0° C. was added NaCN (73.5 mg, 1.500 mmol) in one charge. The reaction mixture was stirred at 10° C. for 12 h. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The resulting 2-(4-bromo-2,3-difluorophenyl)acetonitrile was used in the next step without further purification. TLC (PE/EA=5:1, Rf 0.6): 1H NMR (400 MHz, CDCl3) δ 7.39 (ddd, J=1.8, 6.1, 8.2 Hz, 1H), 7.15 (t, J=6.8 Hz, 1H), 3.78 (s, 2H).

Workup

  1. additioncharge
  2. concentrationThen the solution was concentrated
  3. extractionThe combined organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting 2-(4-bromo-2,3-difluorophenyl)acetonitrile was used in the next step without further purification

Sources & evidence

ORD record
ord-dbb99a7242164d5ea62500511d47f862
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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