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

HRID 1839884Notes

Reaction equation

HRID 1839884 reaction equation
[Br:1][C:2]1[C:3]([CH3:14])=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[S:8][CH2:7][CH2:6][C:5]2=[O:13].[BH4-].[Na+].Cl>CO>[Br:1][C:2]1[C:3]([CH3:14])=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[S:8][CH2:7][CH2:6][CH:5]2[OH:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 152784955,8-Dimethyl-6-bromothiochroman-4-one

Product 1

HCID 234507086-Bromo-5,8-dimethylthiochroman-4-olYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100-ml eggplant type flask, 5.0 g (18.4 mol) of 6-bromo-5,8-dimethylthiochroman-4-one as a halogenated thiochroman-4-one compound was dissolved in 30 ml of methanol, and 0.35 g (9.2 mmol, 0.5 equivalent) of sodium borohydride as a reducing agent was added at room temperature. The reaction mixture was stirred for 2 hours, then, diluted hydrochloric acid was added, and the mixture was extracted with ethyl acetate. An organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then solvent was distilled off to give 0.49 g (yield 95%) of 6-bromo-5,8-dimethylthiochroman-4-ol.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washAn organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationsolvent was distilled off

Sources & evidence

ORD record
ord-7d38227d970f45899c65832f4703a9dd
Source dataset
uspto-grants-2004_01
Patent number
US06677460B1

Reaction notes

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