Bromocyclopentane → 4'-Methanesulfonyl-3,4-dicyclopentyloxy-biphenyl

HRID 1370765Notes

Reaction equation

HRID 1370765 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13](O)[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:19](=[O:22])([O-])[O-].[K+].[K+].[CH:25]1(Br)[CH2:29][CH2:28][CH2:27][CH2:26]1>CC(CC)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[C:13]([O:22][CH:19]3[CH2:7][CH2:6][CH2:5][CH2:10]3)[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 18513227HCID 18513227, compound

Product 1

HCID 101356374'-Methanesulfonyl-3,4-dicyclopentyloxy-biphenylYield 92%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
40 °C

Procedure

4′-methanesulfonyl-biphenyl-3,4-diol (30 mg) and potassium carbonate (38 mg) were dissolved in methylethylketone. Afterward, cyclopentylbromide (51 mg) and tetrabutylammoniumiodide (2-3 mg) were added one after another and heated for 24 hours at 40° C. After filtering just potassium carbonate, the residue was separated through a silica gel attributed chromatography (an eluting agent: ethylacetate/n-hexane=1/1, v/v). As a result, the present compound (37 mg, productive yield 92%) was obtained.

Workup

  1. filtrationAfter filtering just potassium carbonate
  2. customthe residue was separated through a silica gel
  3. customAs a result, the present compound (37 mg, productive yield 92%) was obtained

Sources & evidence

ORD record
ord-d15d76515fa34eca937db22460ab7562
Source dataset
uspto-grants-2003_06
Patent number
US06583321B1

Reaction notes

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