Water → 1-(Phenylethynyl)-4-(phenylsulfonyl)benzene

HRID 2376978

反応式

HRID 2376978 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[CH:2].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]1([C:2]#[C:1][C:3]2[CH:4]=[CH:5][C:6]([S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:10])=[O:11])=[CH:7][CH:8]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 11575IodobenzeneHCID 199393204-Phenylsulfonylphenylethyne

生成物 1

HCID 210994031-(Phenylethynyl)-4-(phenylsulfonyl)benzene収率 28%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒

実験手順

A mixture of 1-ethynyl-4-(phenylsulfonyl)benzene (100 mg, 0.4 mmol), iodobenzene (0.05 mL, 0.44 mmol) and triethylamine (1 mL) in toluene (1 mL) was degassed. Copper(I) iodide (3 mg, 0.004 mmol) and dichlorobis(triphenylphosphine)-palladium(II) (3 mg, 0.004 mmol) were added and the reaction stirred at room temperature overnight. The mixture was poured into water and extracted with ethyl acetate. The organic layer was dried and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (35 mg, 28%). δH (500 MHz, d6 DMSO): 7.97 (4H, dd, J=2.6, 8.4 Hz), 7.77-7.69 (3H, m), 7.64-7.56 (4H, m), 7.43-7.41 (3H, m).

後処理

  1. customwas degassed
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-ba9a3283617640d78ac445ed19ea65b5
出典データセット
uspto-grants-2008_12
特許番号
US07468393B2

関連ノート

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