Water → 4-(3-Bromophenyl)but-3-yn-1-ol

HRID 30566

反応式

HRID 30566 の反応式
I[C:2]1[CH:3]=[C:4]([Br:8])[CH:5]=[CH:6][CH:7]=1.[CH:9]#[C:10][CH2:11][CH2:12][OH:13].C(N(CC)CC)C.O>CN(C=O)C.[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>[Br:8][C:4]1[CH:3]=[C:2]([C:9]#[C:10][CH2:11][CH2:12][OH:13])[CH:7]=[CH:6][CH:5]=1

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 11561Benzene, 1-bromo-3-iodo-HCID 135663-Butyn-1-OL

生成物 1

HCID 218954424-(3-Bromophenyl)but-3-yn-1-ol収率 92%

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 6228Dimethylformamide溶媒

実験手順

A solution of 10.0 gm (35.3 mmol) of 3-iodo-bromobenzene in DMF was treated with 2.95 mL (88 mmol) of 4-butyne-1-ol, 0.2 gm (1.06 mmol) of copper (I) iodide, 1.23 gm of dichlorobis(triphenylphosphine)-palladium(II), and 49 mL (0.35 mol) of triethylamine, stirred at room temperature for 18 h, poured into water and extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried over Na2SO4 and concentrated at reduced pressure. Chromatography of the resultant concentrate on silica gel with a gradient of 5% to 30% EtOAc-hexanes afforded 4-(3-bromophenyl)but-3-yn-1-ol as an orange oil, 7.3 gm (92% yield); 1H NMR (400 MHz, CDCl3) δ: 1.79 (s, 1H), 2.67 (t, 2H, J=6.3 Hz), 3.80 (t, 2H, J=6.3 Hz), 7.14 (t, 1H, J=7.9 Hz), 7.30 (d, 1H, J=7.9 Hz), 7.41 (m, 1H), 7.54 (t, 1H, J=1.6 Hz).

後処理

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed sequentially with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated at reduced pressure
  5. concentrationChromatography of the resultant concentrate on silica gel with a gradient of 5% to 30% EtOAc-hexanes

出典と根拠

ORDレコード
ord-cbe3e1baed484ad6aa1b66bc899ccbd9
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

関連ノート

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