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

HRID 30566

반응식

HRID 30566 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cbe3e1baed484ad6aa1b66bc899ccbd9
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

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