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

HRID 1807588Notes

Reaction equation

HRID 1807588 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 (30 mL) were 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 and concentrated to remove EtOH. The aqueous layer was extracted with EA 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 INT-28 (2.56 g, 85%) as white solid. LCMS-ESI (m/z) calculated for C9H9BrO: 213.1; 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
  3. concentrationconcentrated
  4. customto remove EtOH
  5. extractionThe aqueous layer was extracted with EA
  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-0c3f638df3ad49aa8119ad0514e00912
Source dataset
uspto-grants-2013_01
Patent number
US08357706B2

Reaction notes

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