Potassium Cyanide → 3-Cyano-5-phenyltoluene

HRID 2228017Notes

Reaction equation

HRID 2228017 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]([CH3:19])[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)(=O)=O.[C-:22]#[N:23].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:22]([C:7]1[CH:8]=[C:9]([CH3:19])[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)#[N:23]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 184745743-Trifluoromethanesulfonyloxy-5-phenyltoluene

Product 1

HCID 184745443-Cyano-5-phenyltolueneYield 20%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-trifluoromethanesulfonyloxy-5-phenyltoluene (35.6 g; 0.128 mol), tetrakis(triphenylphosphine)palladium (12 g; 0.01 mol) and KCN (15.11 g; 0.23 mol) in dioxan (300 ml) was heated at reflux under argon an atmosphere for 24 hours. After extraction with ether and evaporating, the residue was purified by flash chromatography eluting with petroleum ether/ethyl acetate (84/6) to give 3-cyano-5-phenyltoluene. Yield=20%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon an atmosphere for 24 hours
  3. extractionAfter extraction with ether
  4. customevaporating
  5. customthe residue was purified by flash chromatography
  6. washeluting with petroleum ether/ethyl acetate (84/6)

Sources & evidence

ORD record
ord-b84c3575c6fd4e799197193abde849e5
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

Loading…