Acetone Cyanohydrin → 3-(2-Bromophenyl)propanenitrile

HRID 2194870Notes

Reaction equation

HRID 2194870 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9]O.CC(C)(O)[C:13]#[N:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1.CCCCCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:13]#[N:14]

Participants

6

Reactant 3

HCID 6406Acetone CyanohydrinHCID 11776TriphenylphosphineHCID 27340892-(2-Bromophenyl)ethan-1-ol

Product 1

HCID 133082983-(2-Bromophenyl)propanenitrile

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

To a solution of commercially available 2-(2-bromophenyl)ethanol (1 eq.) in Benzene (0.064M) at room temperature was added acetone cyanohydrin (1.5 eq), 1-1′(Azodicarbonyl)dipiperidine (1.5 eq) then dropwise over 5 min triphenyl phosphine (1.5 eq). The mixture was stirred at room temperature for 12 h, diluted with hexane (0.03M) and filtered on pad of silica gel. Fractions containing the desired material were combined and concentrated. A second purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 30%, in 30 min) afforded the desired compound as a colorless oil.

Workup

  1. filtrationfiltered on pad of silica gel
  2. additionFractions containing the desired material
  3. concentrationconcentrated
  4. customA second purification by column chromatography on silica gel (Combi-Flash by ISCO)
  5. washeluting with Hex/EtOAc (0 to 30%, in 30 min)

Sources & evidence

ORD record
ord-96318109c5334d4d890db5827bc418ec
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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