Chloroform → HCID 67167626, compound

HRID 389023

Reaction equation

HRID 389023 reaction equation
[Br:1]Br.C(Cl)(Cl)Cl.[S:7]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8]1>O>[Br:1][C:8]1[S:7][C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[O:21])[C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24408BromineHCID 7684929,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one

Product 1

HCID 67167626HCID 67167626, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bromine (8.5 mL, 165 mmol) was added dropwise to a chloroform (300 mL) solution of 9,10-dihydro-1-thiabenzo[f]azulen-4-one (23.2 g, 108 mmol), and the mixture was stirred for 4 hours. Water was added to the reaction mixture, the product was extracted with ethyl acetate, the organic layer was then washed with a saturated aqueous sodium bicarbonate solution and with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvents were distilled off under a reduced pressure, and the residue was purified by silica gel chromatography (hexane-ethyl acetate), to give 22.0 g (69%) of the captioned compound.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washthe organic layer was then washed with a saturated aqueous sodium bicarbonate solution and with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvents were distilled off under a reduced pressure
  5. customthe residue was purified by silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-32bf708a922040b59afc2e4d63b8cc8d
Source dataset
uspto-grants-2013_02
Patent number
US08377967B2

Linked notes

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