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

HRID 30566

Reaktionsgleichung

Reaktionsgleichung von HRID 30566
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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cbe3e1baed484ad6aa1b66bc899ccbd9
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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