Dimethyl Sulfoxide → 2-(3-Bromo-5-methoxyphenyl)acetonitrile

HRID 2069078Notes

Reaction equation

HRID 2069078 reaction equation
[C-:1]#[N:2].[Na+].CS(C)=O.[Br:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[C:11]([CH2:17]Br)[CH:10]=1.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH2:17][C:1]#[N:2])[CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 122764491-Bromo-3-(bromomethyl)-5-methoxybenzene

Product 1

HCID 212429652-(3-Bromo-5-methoxyphenyl)acetonitrileYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Sodium cyanide (3.4 g; WAKO) was added to a DMSO (100 mL) solution of Intermediate 2 (16.3 g) at room temperature and the resulting mixture was stirred at 40° C. for 1 hour and 40 minutes. Ethyl acetate (300 mL) and saturated aqueous sodium bicarbonate solution (150 mL), and water (150 mL) were added to extract the reaction mixture, the reaction mixture was washed with saturated brine (300 mL), the organic layer was dried, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Yamazen; n-hexane/ethyl acetate) to give the title compound (11.37 g).

Workup

  1. extractionto extract the reaction mixture
  2. washthe reaction mixture was washed with saturated brine (300 mL)
  3. customthe organic layer was dried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (Yamazen; n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-403b95ede2c1470c813392e81959ab6c
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

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