Bromine → Ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate

HRID 2296791Notes

Reaction equation

HRID 2296791 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]2[CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:4]=12.[Br:18]Br>C(Cl)(Cl)Cl>[Br:18][CH:15]1[CH2:14][CH2:13][C:5]2=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[S:7][C:3]([S:2][CH3:1])=[C:4]2[C:16]1=[O:17]

Participants

4

Reactant 2

HCID 24408BromineHCID 2778748Ethyl 3-(methylthio)-4-oxo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate

Product 1

HCID 15885619Ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylateYield 87.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Ethyl 4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (25.12 g) was dissolved in chloroform (400 ml); a solution of bromine (15.59 g) in chloroform (20 ml) was added dropwise at room temperature over a period of 30 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-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (28.27 g, 87.1%), which was then recrystallized from ethyl acetate-hexane. Light-yellow prisms. Melting point 147-148° 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-0405aefbf3b749eabf1b67e638a0ae45
Source dataset
uspto-grants-2002_12
Patent number
US06489351B1

Reaction notes

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