Dimethyl Sulfate → 1-Bromo-3-[3-(2-methoxy-ethyl)-cyclobutyl]-benzene

HRID 2240965Notes

Reaction equation

HRID 2240965 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:11][CH:10]([CH2:12][CH2:13][OH:14])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[CH3:17]OS(OC)(=O)=O>C(OCC)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[CH2:9][CH:10]([CH2:12][CH2:13][O:14][CH3:17])[CH2:11]2)[CH:3]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 593052992-[3-(3-Bromo-phenyl)-cyclobutyl]-ethanol

Product 1

HCID 593053151-Bromo-3-[3-(2-methoxy-ethyl)-cyclobutyl]-benzeneYield 74%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

2-[3-(3-Bromo-phenyl)-cyclobutyl]-ethanol (0.500 gm, 1.96 mmol) was dissolved in diethylether (7 mL) and combined with tetrabutylammonium iodide (75 mg, 0.203 mmol), an aqueous solution of sodium hydroxide (5 gm, 50% wt/wt, 62.5 mmol) and dimethylsulfate (0.50 ml, 5.27 mmol). The mixture was stirred overnight at ambient temperature then diluted with diethyl ether and decanted. The supernatant was concentrated onto silica and purified by column chromatography (25% diethylether in hexanes) to afford 389 mg of an oil (74%). This material was used in next step without further characterization.

Workup

  1. customdecanted
  2. concentrationThe supernatant was concentrated onto silica
  3. custompurified by column chromatography (25% diethylether in hexanes)

Sources & evidence

ORD record
ord-b6f9e42fc9614c63ac949be046013eb5
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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