Iodine → HCID 69120067, compound

HRID 2118338Notes

Reaction equation

HRID 2118338 reaction equation
[CH:1]1([S:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9](Br)[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.[I:19]I.S([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH:1]1([S:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([I:19])[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 807IodineHCID 24437Sodium SulfiteHCID 221708791-Bromo-3-(cyclopentylthio)benzeneHCID 178418339Butyllithium

Product 1

HCID 69120067HCID 69120067, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 1-(cyclopentylthio)-3-bromobenzene (3.6 g) in dry THF (40 ml) at −60° under nitrogen was added n-butyl lithium (10 ml, 1.6M in hexanes). After stirring for 15 min a solution of iodine (4.3 g) in dry THF (30 ml) was added dropwise and the solution was allowed to warm to 0°. Wet THF was added to the brown solution, followed by aqueous sodium sulphite. The resulting colourless solution was extracted with diethyl ether and the combined organic extracts were washed with water, brine and dried (Na2SO4). The solvent was evaporated and the residue was purified by column chromatography on silica using cydohexane as eluant. This gave the title compound (1.8 g). LCMS RT=4. 1 min

Workup

  1. additionwas added dropwise
  2. temperatureto warm to 0°
  3. extractionThe resulting colourless solution was extracted with diethyl ether
  4. washthe combined organic extracts were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated
  7. customthe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-1de3e2c7aadd4ff0a8a6296495ef3d36
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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