Bromine → HCID 21699087, compound

HRID 1597167Notes

Reaction equation

HRID 1597167 reaction equation
[CH3:1][S:2][C:3]1[S:8][C:7]2[CH:9]=[CH:10][S:11][C:6]=2[C:5](=[O:12])[CH:4]=1.[Br:13]Br.ClCCl.C(OCC)(=O)C>C(O)(=O)C>[Br:13][C:4]1[C:5](=[O:12])[C:6]2[S:11][CH:10]=[CH:9][C:7]=2[S:8][C:3]=1[S:2][CH3:1]

Participants

5

Reactant 3

HCID 24408BromineHCID 21226138Dichloromethane ethylacetateHCID 21699033HCID 21699033, compound

Product 1

HCID 21699087HCID 21699087, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

5-Methylthio-7-oxo-7H-thieno[3,2-b]thiopyran (2.14 g, 10 mmol) was dissolved in acetic acid (140 ml) and added dropwise with bromine (0.96 ml). The reaction mixture was stirred at 50° C. for 16 hours. The resulting precipitates were collected by filtration, washed with water and dried. The reaction product was purified by column chromatography(Wako Gel™ C-200: dichloromethane-ethyl acetate=15:1) to obtain 1.98 g (yield: 67%) of 6-bromo-5-methylthio-7-oxo-7H-thieno[3,2-b]thiopyran.

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe reaction product was purified by column chromatography(Wako Gel™ C-200

Sources & evidence

ORD record
ord-cc897aac20834398b21875873c1ec4e1
Source dataset
uspto-grants-2001_09
Patent number
US06294527B1

Reaction notes

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