Sulfuric Acid → 7-Bromothiochroman-4-one

HRID 1593032Notes

Reaction equation

HRID 1593032 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:11](=[O:13])[CH2:10][CH2:9][S:8]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 186867493-((3-Bromophenyl)thio)propanoic acid

Product 1

HCID 223357357-Bromothiochroman-4-oneYield 31.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3[(3-bromophenyl)thio]propanoic acid (390 mg) and concentrated sulfuric acid (1.6 ml) was allowed to stand at 20° C. for 4 days. Water was added and the mixture was extracted with ethyl acetate. The organic solution was washed with sodium bicarbonate solution, brine, dried (MgSO4) and evaporated. The residue was purified by chromatography on a silica SPE cartridge (10 g) eluting with cyclohexane, dichloromethane-cyclohexane (1:2, 1:1) and dichloromethane to give the title compound (116 mg) 13C NMR δ (CDCl3) 193.5, 144.4, 131.0, 130.3, 130.0, 128.9, 128.8, 39.6, 27.1.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic solution was washed with sodium bicarbonate solution, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography on a silica SPE cartridge (10 g)
  6. washeluting with cyclohexane, dichloromethane-cyclohexane (1:2, 1:1) and dichloromethane

Sources & evidence

ORD record
ord-c5a12791df464ac09a35f34c77c238c9
Source dataset
uspto-grants-2007_11
Patent number
US07294650B2

Reaction notes

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