1-Bromo-2-nitrobenzene → 4-(2-Nitrophenyl)but-3-yn-1-ol

HRID 342188노트

반응식

HRID 342188 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([OH:15])[CH2:12][C:13]#[CH:14]>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:14]#[C:13][CH2:12][CH2:11][OH:15])([O-:10])=[O:9]

참가 물질

6

반응물 2

HCID 113411-Bromo-2-nitrobenzeneHCID 135663-Butyn-1-OL

생성물 1

HCID 117454514-(2-Nitrophenyl)but-3-yn-1-ol수율 78.5%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8471Triethylamine용매

실험 절차

A solution of o-bromonitrobenzene (8.1 g, 0.04 mol) in 160 ml of triethylamine, under nitrogen, is treated sequentially with bis(triphenylphosphine)palladium(II)chloride (0.28 g, 0.4 mmol), 3-butyne-1-ol (2.81 g, 0.04 mol) and copper(I)iodide (0.15 g, 0.8 mmol), stirred for about 16 hours and filtered. The filtercake is washed with toluene. The filtrates are combined and concentrated in vacuo to give the title product as a dark oil, 6.0 g, 78.5% yield, identified by NMR and mass spectral analyses.

후처리

  1. filtrationfiltered
  2. washThe filtercake is washed with toluene
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-828cf1896fe146b193c3ca0f64405f32
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856576

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