Potassium Cyanide → 3-Cyano-5-phenyltoluene

HRID 2228017ノート

反応式

HRID 2228017 の反応式
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]

参加物

5

反応物 2

HCID 9032Potassium CyanideHCID 184745743-Trifluoromethanesulfonyloxy-5-phenyltoluene

生成物 1

HCID 184745443-Cyano-5-phenyltoluene収率 20%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-b84c3575c6fd4e799197193abde849e5
出典データセット
uspto-grants-2002_07
特許番号
US06414145B1

反応ノート

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