Tetrahydrofuran → 6-bromo-4,7-difluoro-2,3-dihydro-1H-inden-1-ol

HRID 533939Notes

Reaction equation

HRID 533939 reaction equation
[Br:1][C:2]1[C:10]([F:11])=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:12])=[C:4]([F:13])[CH:3]=1.C1COCC1.[BH4-].[Na+]>CCO>[Br:1][C:2]1[C:10]([F:11])=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:12])=[C:4]([F:13])[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 867151266-bromo-4,7-difluoro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 867151256-bromo-4,7-difluoro-2,3-dihydro-1H-inden-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 6-bromo-4,7-difluoro-2,3-dihydro-1H-inden-1-one (0.5 g), THF (1 mL) and EtOH (1 mL) was added NaBH4 (100 mg). After 1 hour the reaction mixture was concentrated and the residue distributed between water and EA. The organic phase was washed with water (3 times), dried (Na2SO4), filtered and concentrated. The residue was purified by preparative HPLC to provide the subtitle compound. MS ESI+: m/z=249 [M+H]+.

Workup

  1. concentrationAfter 1 hour the reaction mixture was concentrated
  2. washThe organic phase was washed with water (3 times)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-e5ef06cd3da54bd6adf90fe761e47c69
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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