1-Indanone, 4-bromo- → 4-Bromo-1-indanol

HRID 1891450Notes

Reaction equation

HRID 1891450 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[BH4-].[Na+]>CCO>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[OH:11]

Participants

4

Reactant 2

HCID 987131-Indanone, 4-bromo-HCID 4311764Sodium borohydride

Product 1

HCID 133302084-Bromo-1-indanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 4-bromoindanone (3 g, 14.2 mmol) in anhydrous EtOH (30mL) was added sodium borohydride (0.36 g, 9.5 mmol) and silica gel (2 g) at 0° C. The reaction was stirred at 0° C. for 20 min and was allowed to stir at room temperature for 2 h. The reaction mixture was quenched with saturated NaHCO3 solution (10 mL) and concentrated to remove EtOH. The aqueous layer was extracted with EA (3×20 mL) and the organic phase was dried over MgSO4. After concentration, the crude product was purified by chromatography (EA/hexane) to yield (±)-4-bromo-2,3-dihydro-1H-inden-1-ol IND INT-5 (2.56 g, 85%) as a white solid. LCMS-ESI (m/z) calculated for C9H9BrO: 213.07; found 195.0 [M−H2O]+, tR=3.07 min. 1H NMR (400 MHz, CDCl3) δ 7.35 (d, J=7.9, 1H), 7.27 (d, J=7.4, 1H), 7.05 (t, J=7.7, 1H), 5.23 (t, J=6.2, 1H), 3.00 (ddd, J=16.6, 8.8, 4.6, 1H), 2.84-2.66 (m, 1H), 2.45 (dddd, J=13.2, 8.4, 7.0, 4.6, 1H), 1.96-1.70 (m, 2H).

Workup

  1. stirringto stir at room temperature for 2 h
  2. customThe reaction mixture was quenched with saturated NaHCO3 solution (10 mL)
  3. concentrationconcentrated
  4. customto remove EtOH
  5. extractionThe aqueous layer was extracted with EA (3×20 mL)
  6. dry with materialthe organic phase was dried over MgSO4
  7. concentrationAfter concentration
  8. customthe crude product was purified by chromatography (EA/hexane)

Sources & evidence

ORD record
ord-06905858d0d74f3cb84dd157b268a1e3
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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