Borane;tetrahydrofuran → (5-Fluoro-2-nitrophenyl)methanol

HRID 1670722Notes

Reaction equation

HRID 1670722 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].B.C1COCC1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH2:7][OH:8])[CH:10]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 12016493(5-Fluoro-2-nitrophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-fluoro-2-nitrobenzoic acid (4.58 g) in THF (50 ml) was added a 1 M solution of BH3.THF in THF (62 ml) while cooling with an ice-bath. The cooling bath was removed and stirring was continued for 1 h at ambient temperature, followed by refluxing for 4 h. The reaction mixture was cooled and MeOH was added to destroy the excess of borane. The mixture was concentrated and water and ethyl acetate were added to the residue. The organic layer was washed with brine, dried and concentrated. Yield: 4.3 g.

Workup

  1. temperaturewhile cooling with an ice-bath
  2. customThe cooling bath was removed
  3. temperatureby refluxing for 4 h
  4. temperatureThe reaction mixture was cooled
  5. additionMeOH was added
  6. customto destroy the excess of borane
  7. concentrationThe mixture was concentrated
  8. additionwater and ethyl acetate were added to the residue
  9. washThe organic layer was washed with brine
  10. customdried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-c2f22035382e457aa1311b9de717b6cd
Source dataset
uspto-grants-2011_08
Patent number
US07994189B2

Reaction notes

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