Sodium borohydride → 4-Bromo-6-fluoro-2,3-dihydro-1H-inden-1-ol

HRID 574633Notes

Reaction equation

HRID 574633 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12].[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[OH:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117702304-bromo-6-fluoro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 894444374-Bromo-6-fluoro-2,3-dihydro-1H-inden-1-olYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to Scheme 2, step 1: To a solution of 4-Bromo-6-fluoro-indan-1-one (10.0 g, 43.7 mmol) in ethanol (183 ml) at 0° C. NaBH4 (3.67 g, 97.0 mmol) was added in portions and then the mixture was stirred at room temperature for 18 h. After evaporation of solvents in vacuo, water was added to the residue, the solution was extracted 3 times with ethyl acetate, then 2N aqueous HCl was added and the combined organic layers were washed with saturated aq. NaHCO3 and water. After drying over Na2SO4 and filtration, solvents were evaporated in vacuo to give 10.0 g of 4-Bromo-6-fluoro-indan-1-ol (4a) which was used immediately in the next step without purification.

Workup

  1. customat 0° C
  2. customAfter evaporation of solvents in vacuo, water
  3. additionwas added to the residue
  4. extractionthe solution was extracted 3 times with ethyl acetate
  5. addition2N aqueous HCl was added
  6. washthe combined organic layers were washed with saturated aq. NaHCO3 and water
  7. dry with materialAfter drying over Na2SO4 and filtration, solvents
  8. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-d79fef12805943159f06ba839ae774d5
Source dataset
uspto-grants-2015_05
Patent number
US09034897B2

Reaction notes

Loading…