6-Bromohexylbut-3-ynyl ether → 1-{4-[(6-Bromohexyl)oxy]-1-butyn-1-yl}-3-(cyclopentylsulfonyl)benzene

HRID 2118344Notes

Reaction equation

HRID 2118344 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[CH:12].[CH:13]1([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23](I)[CH:22]=2)(=[O:20])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1>CC#N.C(N(CC)CC)C.[Cu](I)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:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[C:12][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([S:18]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:20])=[O:19])[CH:22]=1

Participants

7

Reactant 2

HCID 113792816-Bromohexylbut-3-ynyl etherHCID 691197141-(Cyclopentylsulfonyl)-3-iodobenzene

Product 1

HCID 691198231-{4-[(6-Bromohexyl)oxy]-1-butyn-1-yl}-3-(cyclopentylsulfonyl)benzene

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 4-[(6-bromohexyl)oxy]-1-butyne (DE 3513885 A1) (288.9 mg) and 1-(cyclopentylsulfonyl)-3-iodobenzene (500 mg) in MeCN (20 ml) and triethylamine (345 μl) was treated with copper iodide (11.78 mg) and dichlorobis(triphenylphosphine)palladium(II) (43.4 mg) and stirred at room temperature for 3 h. The reaction mixture was partitioned between EtOAc and water, the organic phase was dried (MgSO4) and concentrated in vacuo. The mixture was purified by column chromatography (SPE bond elut, gradient 0 to 40% diethyl ether in cyclohexane) to afford the title compound.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. dry with materialthe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe mixture was purified by column chromatography (SPE bond elut, gradient 0 to 40% diethyl ether in cyclohexane)

Sources & evidence

ORD record
ord-2c07afdb60d3435aba64de0bcabd2747
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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