Water → HCID 18509289, compound

HRID 1356691Notes

Reaction equation

HRID 1356691 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:11]=[CH:10][C:9]([S:12][C:13]#N)=[CH:8][C:5]=1[C:6]#[N:7].CI.O>C(O)C>[F:3][C:4]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 4311764Sodium borohydrideHCID 18509275HCID 18509275, compound

Product 1

HCID 18509289HCID 18509289, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of sodium borohydride (90%, 0.41 g (9.76 mmol)) in ethanol (10 ml), 2-fluoro-5-(thiocyanato)benzonitrile (0.29 g (1.63 mmol)) was added with stirring under cooling with ice. To the resulting mixture, after one hour's stirring at room temperature, methyl iodide (0.11 ml (1.71 mmol)) was added and the resulting mixture was stirred overnight at room temperature. Then, the reaction mixture was poured into water and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (3:7) as eluent, to give 0.25 g (92%) of 2-fluoro-5-(methylthio)benzonitrile as pale yellow-white crystals.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringTo the resulting mixture, after one hour's stirring at room temperature
  4. stirringthe resulting mixture was stirred overnight at room temperature
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-64516dc73e3c4524aa07aa4bb1a50d7f
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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