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

HRID 469159Notes

Reaction equation

HRID 469159 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-10cb1f4f0d3c4988ba3d4031e0193416
Source dataset
uspto-grants-2014_01
Patent number
US08629102B2

Reaction notes

Loading…