Water → HCID 18388321, compound

HRID 1936859Notes

Reaction equation

HRID 1936859 reaction equation
[CH:1]([S:4][C:5]1[S:9][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:7]2[CH2:15][CH2:16][CH2:17][C:18](=[O:19])[C:6]=12)([CH3:3])[CH3:2].[Br:20]Br.O>CO>[Br:20][CH:17]1[CH2:16][CH2:15][C:7]2=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:9][C:5]([S:4][CH:1]([CH3:2])[CH3:3])=[C:6]2[C:18]1=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 2820027ethyl 4-oxo-3-propan-2-ylsulfanyl-6,7-dihydro-5H-2-benzothiophene-1-carboxylate

Product 1

HCID 18388321HCID 18388321, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Ethyl 4,5,6,7-tetrahydro-3-isopropylthio-4-oxobenzo[c]thiophene-1-carboxylate (2.50 g) was dissolved in methanol (80 ml); a solution of bromine (1.34 g) in methanol (8.6 ml) was added dropwise at room temperature. After the reaction mixture was stirred at room temperature for 2 hours, it was poured over water and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium thiosulfate, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:5, v/v) to yield ethyl 5-bromo-4,5,6,7-tetrahydro-3-isopropylthio-4-oxobenzo[c]thiophene-1-carboxylate (2.65 g, 83.9%), which was then recrystallized from ethyl acetate-hexane. Colorless prisms. Melting point 107-108° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous solution of sodium thiosulfate
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4)
  4. distillationafter which the solvent was distilled off
  5. washeluted with ethyl acetate-hexane (1:5

Sources & evidence

ORD record
ord-24d4462c7e2747b9aaffa54f5716c218
Source dataset
uspto-grants-2002_05
Patent number
US06391905B1

Reaction notes

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