Potassium Phosphate, Tribasic → 7-{4-[(6-Bromohexyl)oxy]butyl}thiochromane 1,1-dioxide

HRID 1593034Notes

Reaction equation

HRID 1593034 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH:11]=[CH2:12].C12BC(CCC1)CCC2.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:31]1[CH:40]=[C:39]2[C:34]([CH2:35][CH2:36][CH2:37][S:38]2(=[O:42])=[O:41])=[CH:33][CH:32]=1>O1CCCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:31]1[CH:40]=[C:39]2[C:34]([CH2:35][CH2:36][CH2:37][S:38]2(=[O:42])=[O:41])=[CH:33][CH:32]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 789669-Borabicyclo(3.3.1)nonaneHCID 694442257-bromo-3,4-dihydro-2H-1lambda6-benzothiopyran-1,1-dioneHCID 858619736-Bromohexylbut-3-enyl ether

Product 1

HCID 694461627-{4-[(6-Bromohexyl)oxy]butyl}thiochromane 1,1-dioxideYield 37.9%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-[(6-bromohexyl)oxy]but-1-ene (180 mg) in tetrahydrofuran (0.6 ml) was added a 0.5M solution of 9-borabicyclo[3.3.1]nonane in tetrahydrofuran (1.8 ml). The solution was stirred at room temperature, under nitrogen for 2 h. Tripotassium phosphate (324 mg) in water (0.46 ml) was added, followed by 7-bromothiochromane 1,1-dioxide (200 mg), palladium (II) acetate (2 mg) and triphenylphosphine (4 mg). The resultant mixture was heated at 60° C. for 17 h. Water was added and the organic layer washed with brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography on a Biotage cartridge (40 g) eluting with cyclohexane-ethyl acetate (1:1) to give the title compound (121 mg) LCMS RT=3.66 min

Workup

  1. washthe organic layer washed with brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by chromatography on a Biotage cartridge (40 g)
  5. washeluting with cyclohexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-3f4b8a78d13c4b79830d5f03fae834d2
Source dataset
uspto-grants-2007_11
Patent number
US07294650B2

Reaction notes

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