Sodium borohydride → 4-bromo-7-fluoro-2,3-dihydro-1H-inden-1-ol

HRID 2170929Notes

Reaction equation

HRID 2170929 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:14]>C(O)(C)C>[Br:3][C:4]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2[OH:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 534401624-Bromo-7-fluoroindan-1-one

Product 1

HCID 896215154-bromo-7-fluoro-2,3-dihydro-1H-inden-1-ol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Reaction under argon atmosphere: to a mixture of 1.69 g (43.7 mmol) of sodium borohydride in 120 ml isopropyl alcohol is added 20.0 g (87.3 mmol) of 4-bromo-7-fluoro-1-indanone portionwise. The reaction mixture is stirred at r.t. for 2 h. The solvent is evaporated. To the residue are added 100 g ice and 200 ml 1N aq. HCl. The mixture is extracted with EtOAc. The combined organic layers are washed with brine, dried and the solvent is evaporated. The residue is chromatographed on silica gel (PE/EtOAc=100/0→70/30) to give the title compound. Yield: 15.4 g; LC (method 4): tR=3.05 min; Mass spectrum (ESI+): m/z=213 [M+H—H2O]+.

Workup

  1. customReaction under argon atmosphere
  2. customThe solvent is evaporated
  3. additionTo the residue are added 100 g ice and 200 ml 1N aq. HCl
  4. extractionThe mixture is extracted with EtOAc
  5. washThe combined organic layers are washed with brine
  6. customdried
  7. customthe solvent is evaporated
  8. customThe residue is chromatographed on silica gel (PE/EtOAc=100/0→70/30)

Sources & evidence

ORD record
ord-4ba6147d4a2546a2bea4b043aead1fde
Source dataset
uspto-grants-2015_06
Patent number
US09051289B2

Reaction notes

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