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

HRID 342188ノート

反応式

HRID 342188 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-828cf1896fe146b193c3ca0f64405f32
出典データセット
uspto-grants-1999_01
特許番号
US05856576

反応ノート

読み込み中…