Water → 1-Bromo-2-(cyclobutylsulfanyl)benzene

HRID 1919866Notes

Reaction equation

HRID 1919866 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[SH:10].CC1C=CC(S(O[CH:22]2[CH2:25][CH2:24][CH2:23]2)(=O)=O)=CC=1.O>CN(C=O)C>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH:22]1[CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 805982-BromobenzenethiolHCID 12621595Cyclobutyl 4-methylbenzene-1-sulfonate

Product 1

HCID 177500921-Bromo-2-(cyclobutylsulfanyl)benzeneYield 58.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 390 mg, 9.75 mmol) in anhydrous DMF (20 mL) was added 2-bromobenzenethiol (1.03 mL, 8.37 mmol) dropwise over 5 minutes. After stirring for 10 minutes at room temperature a solution of cyclobutyl 4-methylbenzenesulfonate (2.0 g, 8.85 mmol) in dry DMF (3 mL) was added dropwise. The resulting solution was then stirred for 2 hours at room temperature, and 2 hours at 50° C. Water was then added, and the mixture extracted with ethyl acetate (×3). The combined organics were washed with brine (×3), then dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel (eluting with neat petrol) to give (2-bromophenyl)(cyclobutyl)sulfane (1.19 g, 4.89 mmol, 58%) as a colourless oil.

Workup

  1. additionwas added dropwise
  2. custom2 hours
  3. customat 50° C
  4. extractionthe mixture extracted with ethyl acetate (×3)
  5. washThe combined organics were washed with brine (×3)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel (eluting with neat petrol)

Sources & evidence

ORD record
ord-8ca31bb55d5b4490bb8b99c39ad22b93
Source dataset
uspto-grants-2012_05
Patent number
US08168673B2

Reaction notes

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