Sodium Cyanide → 1-Cyano-3-(4'-fluoro-4-biphenylyl)-butan-3-ol

HRID 1439766Notes

Reaction equation

HRID 1439766 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)([OH:6])[CH3:5].[C-:20]#[N:21].[Na+]>CS(C)=O>[C:20]([CH2:2][CH2:3][C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)([OH:6])[CH3:5])#[N:21]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 203028961-Chloro-3-(4'-fluoro-4-biphenylyl)-butan-3-ol

Product 1

HCID 213964731-Cyano-3-(4'-fluoro-4-biphenylyl)-butan-3-ol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 27.9 g. of 1-chloro-3-(4'-fluoro-4-biphenylyl)-butan-3-ol in 60 ml. of dimethylsulfoxide is added, at 80°, to a solution of 7.6 g. of NaCN in 100 ml. of dimethylsulfoxide. The mixture is warmed to 80°-90° for 6 hours, poured onto ice and worked up in the customary manner to give 1-cyano-3-(4'-fluoro-4-biphenylyl)-butan-3-ol, m.p. 118°-120°.

Workup

  1. temperatureThe mixture is warmed to 80°-90° for 6 hours
  2. additionpoured onto ice

Sources & evidence

ORD record
ord-63c8ba5920a94058a8589f9c5fcba36a
Source dataset
uspto-grants-1977_11
Patent number
US04060633

Reaction notes

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