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

HRID 1729449

反応式

HRID 1729449 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 retool) in dry toluene (5 mL) under N2 was added 2-bromo-5-ni tro-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 liltrate 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 MMz, CDCl3) δ 2.42 (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 liltrate 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-17d68daed44e47689303f3c6fa0c53da
出典データセット
uspto-grants-1994_07
特許番号
US05332744

関連ノート

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