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

HRID 923726Notes

Reaction equation

HRID 923726 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+]>C(O)C>[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-indanolYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound 2 (435 g, 2.06 mol, 1 equiv) in ethanol (5 L) was treated with sodium borohydride (101.6 g, 2.68 mol, 1.3 equiv) and stirred overnight at room temperature. The reaction was concentrated under reduced pressure and the residue partitioned between 4 L of dichloromethane and 4 L of 10% aqueous hydrochloric acid. The layers were separated and the aqueous layer was extracted with dichloromethane (3×1 L). The combined organic layers were washed with saturated brine (2 L), dried over sodium sulfate and concentrated under reduced pressure. The resulting solid was dried overnight in a vacuum oven at 30° C. to give compound 3 (422 g, 96% yield) as an off-white solid.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue partitioned between 4 L of dichloromethane and 4 L of 10% aqueous hydrochloric acid
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (3×1 L)
  5. washThe combined organic layers were washed with saturated brine (2 L)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting solid was dried overnight in a vacuum oven at 30° C.

Sources & evidence

ORD record
ord-a30a5568944243e682bed3f7cb1caa3c
Source dataset
uspto-grants-2016_03
Patent number
US09279024B2

Reaction notes

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