Potassium Carbonate → 1-Bromo-3-(cyclopentylthio)benzene

HRID 2118337Notes

Reaction equation

HRID 2118337 reaction equation
I[CH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[Br:7][C:8]1[CH:9]=[C:10]([SH:14])[CH:11]=[CH:12][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([S:14][CH:2]2[CH2:6][CH2:5][CH2:4][CH2:3]2)[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73784Iodocyclopentane2×HCID 80597m-Bromobenzenethiol

Product 1

HCID 221708791-Bromo-3-(cyclopentylthio)benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Iodocyclopentane (3.93 ml) was added to a mixture of 3-bromobenzenethiol and potassium carbonate (5.4 g) in acetone (50 ml) and the reaction was stirred under nitrogen for 1.5 h. A further portion of iodocyclopentane (2 ml) was added and the mixture was stirred for 1 h. The solvent was evaporated and the residue was partitioned between water and EtOAc. he combined organic extracts were washed with NaOH (2N), brine and dried (Na2SO4). The resulting oil was purified using biotage™ chromatography on silica using cyclohexane as eluant to give the title compound (3.6 g). LCMS RT=4.1 min

Workup

  1. stirringthe mixture was stirred for 1 h
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water and EtOAc
  4. washwere washed with NaOH (2N), brine
  5. dry with materialdried (Na2SO4)
  6. customThe resulting oil was purified

Sources & evidence

ORD record
ord-78e56b6fa0b9497ab5b70c5aeb758eea
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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