Stannane, trimethyl(4-methylphenyl)- → 2-Cyano-4'-methyl-4-nitrobiphenyl

HRID 1029600

反応式

HRID 1029600 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([Sn](C)(C)C)=[CH:3][CH:2]=1.Br[C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[C:15]#[N:16]>C1(C)C=CC=CC=1.CCOC(C)=O.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:15]([C:14]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:13]=1[C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)#[N:16]

参加物

6

反応物 2

HCID 617834Stannane, trimethyl(4-methylphenyl)-HCID 70954232-Bromo-5-nitrobenzonitrile

生成物 1

HCID 190122062-Cyano-4'-methyl-4-nitrobiphenyl収率 74%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of p-tolyltrimethyltin (389 mg, 1.525 mmol) in dry toluene (5 mL) under N2 was added 2-bromo-5-nitro-benzonitrile (276 mg, 1.22 mmol) and Pd(PPh3)4 (176 mg; 10 mol %). The reaction was stirred at reflux under N2 for 24 hours and then cooled to room temperature. The mixture was diluted with EtOAc and the solid was removed by filtration through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on a silica column eluting with Hex/EtOAc (10:1) to afford 214 mg (74%) of the titled compound as a slightly yellow solid. 1H NMR (300 MHz, CDCl3) δ2.42 (s, 3H), 7.32 (d, 2H), 7.48 (d, 2H), 7.69 (d, 1H), 8.45 (dd, 1H), 8.61 (s, 1H).

後処理

  1. temperatureat reflux under N2 for 24 hours
  2. customthe solid was removed by filtration through a pad of celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography on a silica column
  5. washeluting with Hex/EtOAc (10:1)

出典と根拠

ORDレコード
ord-02022cdec117434283cb4d00831fa305
出典データセット
uspto-grants-1992_04
特許番号
US05102880

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