Bromine → HCID 18388324, compound

HRID 1108330Notes

Reaction equation

HRID 1108330 reaction equation
[O:1]=[C:2]1[C:10]2[C:6](=[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:8][C:9]=2[S:11][CH2:12][CH2:13][CH3:14])[CH2:5][CH2:4][CH2:3]1.[Br:20]Br>C(Cl)(Cl)Cl>[Br:20][CH:3]1[CH2:4][CH2:5][C:6]2=[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:8][C:9]([S:11][CH2:12][CH2:13][CH3:14])=[C:10]2[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 2778813Ethyl 4-oxo-3-(propylsulfanyl)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxylate

Product 1

HCID 18388324HCID 18388324, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Ethyl 4,5,6,7-tetrahydro-4-oxo-3-propylthiobenzo[c]thiophene-1-carboxylate (25.29 g) was dissolved in chloroform (380 ml); a solution of bromine (13.81 g) in chloroform (20 ml) was added dropwise at room temperature over a period of 20 minutes. After the reaction mixture was stirred at room temperature for 40 minutes, it was washed with a 2% aqueous solution of sodium sulfite (400 ml), water, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4), after which the solvent was distilled off to yield ethyl 5-bromo-4,5,6,7-tetrahydro-4-oxo-3-propylthiobenzo[c]thiophene-1-carboxylate (29.07 g, 90.9%), which was then recrystallized from ethyl acetate-hexane. Light-yellow prisms. Melting point 93-94° C.

Workup

  1. washit was washed with a 2% aqueous solution of sodium sulfite (400 ml), water
  2. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4)
  3. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-4a3fc9ecce8543b6bc21ea95a1d9ec37
Source dataset
uspto-grants-2000_05
Patent number
US06066658

Reaction notes

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