Hydrochloric Acid → 6-Bromo-4,5,8-trimethylthiochroman-4-ol

HRID 964385Notes

Reaction equation

HRID 964385 reaction equation
[CH3:1]Br.[Mg].[Br:4][C:5]1[C:6]([CH3:17])=[C:7]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[S:11][CH2:10][CH2:9][C:8]2=[O:16].Cl>O1CCCC1>[Br:4][C:5]1[C:6]([CH3:17])=[C:7]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[S:11][CH2:10][CH2:9][C:8]2([CH3:1])[OH:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 152784955,8-Dimethyl-6-bromothiochroman-4-oneHCID 86584079Magnesium methylbromide

Product 1

HCID 234506886-Bromo-4,5,8-trimethylthiochroman-4-olYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 300-ml three-necked flask was charged with 55 ml (55 mmol, 3 equivalents) of a 1M solution of magnesium methyl bromide (MeMgBr) and 100 ml of tetrahydrofuran (THF), and the mixture was cooled with ice under nitrogen current. To this mixture was dropwise added a solution of 5.0 g (18.4 mmol) of 6-bromo-5,8-dimethylthiochroman-4-one in 15 ml of THF, and the mixture was stirred at room temperature for 3 hours and then refluxed for 2 hours. To the reaction mixture was added 5% HCl, and the mixture was extracted with ethyl acetate. The resultant organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off to give 5.2 g (yield 99%) of 6-bromo-4,5,8-trimethylthiochroman-4-ol.

Workup

  1. temperaturethe mixture was cooled with ice under nitrogen current
  2. temperaturerefluxed for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe resultant organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-7e465c63f72b489b86598cfdb4d67280
Source dataset
uspto-grants-1998_06
Patent number
US05767289

Reaction notes

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