Water → 7-Bromothiochromane

HRID 1593033Notes

Reaction equation

HRID 1593033 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH2:7][CH2:8][S:9]2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.O>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][S:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12052TriethylsilaneHCID 223357357-Bromothiochroman-4-one

Product 1

HCID 189663587-BromothiochromaneYield 100.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-bromo-2,3-dihydro-4H-thiochromen-4-one (1 g) in trifluoroacetic acid (12 ml) was treated with triethylsilane (1.48 ml) and the mixture was stirred at reflux for 4 h. Water was added and the mixture extracted with ethyl acetate. The organic solution was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography on a Biotage cartridge (40 g) eluting with petrol-diethyl ether (10:1) to give the title compound (946 mg). LCMS RT=3.71 min

Workup

  1. temperatureat reflux for 4 h
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic solution was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by chromatography on a Biotage cartridge (40 g)
  7. washeluting with petrol-diethyl ether (10:1)

Sources & evidence

ORD record
ord-fe8c8c3b05fe45f580536c6c2d2f17e7
Source dataset
uspto-grants-2007_11
Patent number
US07294650B2

Reaction notes

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