1-Iodo-3-nitrobenzene → 1-{4-[(6-Bromohexyl)oxy]but-1-ynyl}-3-nitrobenzene

HRID 857087Notes

Reaction equation

HRID 857087 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[CH2:11]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][Br:22])[CH2:12][C:13]#[CH:14]>CN(C=O)C.C(N(C(C)C)CC)(C)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>[Br:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][O:15][CH2:11][CH2:12][C:13]#[C:14][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1

Participants

7

Reactant 2

HCID 125741-Iodo-3-nitrobenzeneHCID 113792816-Bromohexylbut-3-ynyl ether

Product 1

HCID 218670991-{4-[(6-Bromohexyl)oxy]but-1-ynyl}-3-nitrobenzeneYield 96.5%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1-iodo-3-nitrobenzene (3 g), 6-bromohexyl but-3-ynyl ether (3 g), bis(triphenylphosphine)palladium (II) chloride (0.421 g), copper (I) iodide (0.114 g) in DMF (10 ml) and diisopropylethylamine (4 ml) was stirred under nitrogen at 20° C. for 5 h. The mixture was concentrated under reduced pressure and the residue was diluted in EtOAc and washed with 2M HCl, NaHCO3, brine and dried (MgSO4). The solvent was removed by evaporation and the residue was chromatographed on a Biotage column eluting with ether:petroleum ether(40–60° C.) (1:9) to give the title compound (4.12 g). LCMS RT=4.14 min

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was diluted in EtOAc
  3. washwashed with 2M HCl, NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. customthe residue was chromatographed on a Biotage column
  7. washeluting with ether

Sources & evidence

ORD record
ord-e5adf66f798e491ba931f560693d866e
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

Loading…