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

HRID 1049987Notes

Reaction equation

HRID 1049987 reaction equation
[C-:1]#[N:2].[Na+].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]Br)=[C:7]([F:13])[CH:6]=1>CN(C=O)C>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:1]#[N:2])=[C:7]([F:13])[CH:6]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrileYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
26 °C

Procedure

A suspension of NaCN (2.085 g, 42.5 mmol) in DMF (20 mL) was added to a solution of 4-bromo-1-(bromomethyl)-2-fluorobenzene (5.7 g, 21.27 mmol) in DMF (20 mL). The mixture was stirred at 26° C. for 10 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-fluorophenyl)acetonitrile (4.01 g, 18.74 mmol, 88.0% yield) was used to next step without further purification. TLC (PE/EA=1/1, Rf 0.5): 1H NMR (400 MHz, CDCl3) δ 7.24-7.37 (m, 3H), 3.70 (s, 2H).

Workup

  1. concentrationThen the solution was concentrated
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-be2626e39b864ebd8afbed43148b1f97
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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