Bromine → HCID 22118464, compound

HRID 1275452Notes

Reaction equation

HRID 1275452 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:18])=[C:8]2[C:13](=[C:14]([CH3:16])[CH:15]=1)[S:12][CH2:11][CH2:10][C:9]2=[O:17])=[O:5])[CH3:2].[Br:19]Br>C(O)C>[Br:19][CH:10]1[C:9](=[O:17])[C:8]2[C:13](=[C:14]([CH3:16])[CH:15]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:7]=2[CH3:18])[S:12][CH2:11]1

Participants

4

Reactant 2

HCID 24408BromineHCID 22118435HCID 22118435, compound

Product 1

HCID 22118464HCID 22118464, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.9 Grams (7.2 mmol) of 6-ethoxycarbonyl-5,8-dimethylthiochroman-4-one was dissolved in 28 ml of ethanol. Then, 1.2 g (7.5 mmol) of bromine was dropwise added with an ice bath cooling, and the mixture was stirred at the same temperature for 1 hour, then the ice bath was removed and further stirred for 1 hour. Water was added to the reaction mixture, and the reaction mixture was extracted with chloroform three times. An organic layer was washed with a saturated sodium chloride aqueous solution three times, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 2.4 g (yield 97%) of the titled compound.

Workup

  1. temperaturecooling
  2. customthe ice bath was removed
  3. stirringfurther stirred for 1 hour
  4. additionWater was added to the reaction mixture
  5. extractionthe reaction mixture was extracted with chloroform three times
  6. washAn organic layer was washed with a saturated sodium chloride aqueous solution three times
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a4aa3723a20f46d3a4cbe558a0a7603c
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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