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

HRID 342188Notes

Reaction equation

HRID 342188 reaction equation
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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-828cf1896fe146b193c3ca0f64405f32
Source dataset
uspto-grants-1999_01
Patent number
US05856576

Reaction notes

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