Bromine → HCID 18388329, compound

HRID 1108332Notes

Reaction equation

HRID 1108332 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-5b79c3c89f0745d09016967417c0a2ea
Source dataset
uspto-grants-2000_05
Patent number
US06066658

Reaction notes

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