Hydrochloric Acid → 5-bromo-2,3-dihydro-1H-inden-1-ol

HRID 1615451Notes

Reaction equation

HRID 1615451 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[BH4-].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH2:6][CH2:5]2

Participants

5

Procedure

5-bromo-2,3-dihydro-1H-inden-1-one (2.0 g) was dissolved in methanol (20 mL), and to the resultant solution, sodium borohydride (0.54 g) was added at room temperature, followed by stirring the resultant reaction mixture at room temperature for 14 hours. To the reaction mixture, 1M hydrochloric acid (50 mL) was added, followed by extracting the resultant reaction mixture with ethyl acetate (50 mL) three times, and the organic phase was washed sequentially with water (50 mL) and a saturated saline (50 mL) and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure to obtain the subject compound (2.0 g) as a pale yellow solid.

Workup

  1. customreaction mixture at room temperature for 14 hours
  2. extractionby extracting the resultant
  3. customreaction mixture with ethyl acetate (50 mL) three times
  4. washthe organic phase was washed sequentially with water (50 mL)
  5. dry with materiala saturated saline (50 mL) and was dried over anhydrous sodium sulfate
  6. distillationFrom the organic phase, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e38b20dd2fd54bdaae32cd3ea815bec8
Source dataset
uspto-grants-2014_07
Patent number
US08765752B2

Reaction notes

Loading…