Sodium Cyanide → 2-(2-(Methylthio)phenyl)acetonitrile

HRID 440542Notes

Reaction equation

HRID 440542 reaction equation
P(Br)(Br)Br.[CH3:5][S:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9]O.[C-:15]#[N:16].[Na+]>C1(C)C=CC=CC=1.O.C(O)C>[CH3:5][S:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][C:15]#[N:16]

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 24614Phosphorus tribromideHCID 3551404(2-Methylsulfanylphenyl)methanol

Product 1

HCID 130200632-(2-(Methylthio)phenyl)acetonitrile

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

Phosphorus tribromide (75 g) in toluene (50 ml) was added to a stirred mixture of 2-methylthiobenzyl alcohol (42.5 g) in toluene (25 ml) over 10 minutes at 5° C. The mixture was then stirred at 40° C. for 1 hour, water (100 ml) was added and stirring continued at ambient temperature for 1 hour. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers yielded an oil. The oil (58.6 g) was dissolved in a 1:2 mixture of water and ethanol and sodium cyanide (26.5 g) was added over 15 minutes. The mixture was stirred at 50° C. for 1.5 hours then poured onto water (500 ml) and extracted with ethyl acetate. The extract yielded 2-methylthiophenylacetonitrile.

Workup

  1. stirringstirring
  2. waitcontinued at ambient temperature for 1 hour
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. customThe combined organic layers yielded an oil
  6. additionwas added over 15 minutes
  7. stirringThe mixture was stirred at 50° C. for 1.5 hours
  8. additionthen poured onto water (500 ml)
  9. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-2bbfef484914458e8f84be195ffb7257
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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