Sodium Chloride → 2-(4-Bromo-2,6-difluorophenyl)acetonitrile

HRID 1525917Notes

Reaction equation

HRID 1525917 reaction equation
[C-:1]#[N:2].[K+].[Br:4][C:5]1[CH:6]=[C:7]([F:14])[C:8]([CH2:12]Br)=[C:9]([F:11])[CH:10]=1.[Cl-].[Na+]>CS(C)=O>[Br:4][C:5]1[CH:6]=[C:7]([F:14])[C:8]([CH2:12][C:1]#[N:2])=[C:9]([F:11])[CH:10]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 9032Potassium CyanideHCID 27733055-Bromo-2-(bromomethyl)-1,3-difluorobenzene

Product 1

HCID 27733112-(4-Bromo-2,6-difluorophenyl)acetonitrileYield 52%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of potassium cyanide (0.55 g, 8.4 mmol) in dimethyl sulfoxide (10 mL) at 23° C. was slowly added 5-bromo-2-(bromomethyl)-1,3-difluorobenzene (2 g, 7.0 mmol), and the reaction mixture was stirred for 3 h. The reaction mixture was poured into saturated aqueous sodium chloride (100 mL) and was extracted with ether (3×100 mL). The combined organic layers were washed with saturated aq sodium chloride (3×50 mL), dried over anhydrous sodium sulfate, and concentrated to dryness. Purification of the residue by flash chromatography (0-100% ethyl acetate/hexanes) afforded the title product (0.84 g, 52%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.04 (s, 2 H) 7.60-7.62 (m, 1 H) 7.62-7.65 (m, 1 H).

Workup

  1. extractionwas extracted with ether (3×100 mL)
  2. washThe combined organic layers were washed with saturated aq sodium chloride (3×50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated to dryness
  5. customPurification of the residue by flash chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-21909970d4534906a3a4aa12bd5aad4f
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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