Bromine → HCID 18388329, compound

HRID 2296793Notes

Reaction equation

HRID 2296793 reaction equation
[CH3:1][S:2][C:3]1[O: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])[O:7][C:3]([S:2][CH3:1])=[C:4]2[C:16]1=[O:17]

Participants

4

Reactant 2

HCID 24408BromineHCID 18388310HCID 18388310, compound

Product 1

HCID 18388329HCID 18388329, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Ethyl 4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]furan-1-carboxylate (4.26 g) was dissolved in chloroform (75 ml); a solution of bromine (2.73 g) in chloroform (5 ml) was added dropwise at room temperature over a period of 10 minutes. After the reaction mixture was stirred at room temperature for 30 minutes, it was washed with a 2% aqueous solution of sodium sulfite (100 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]furan-1-carboxylate (5.01 g, 89.8%), which was then recrystallized from ethyl acetate-hexane. Colorless needles. Melting point 130-131° C.

Workup

  1. washit was washed with a 2% aqueous solution of sodium sulfite (100 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-ae3f979750cb445fb9a5d58556a17f62
Source dataset
uspto-grants-2002_12
Patent number
US06489351B1

Reaction notes

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