3-Amino-4-fluorobenzoic acid → (3-Amino-4-fluorophenyl)methanol

HRID 1058676Notes

Reaction equation

HRID 1058676 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5](O)=[O:6].B.C1COCC1>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 753963-Amino-4-fluorobenzoic acidHCID 2723981Borane;tetrahydrofuran2×

Product 1

HCID 13563644(3-Amino-4-fluorophenyl)methanolYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-4-fluorobenzoic acid (15 g, 97 mmol) in THF at 0° C. was treated with 1.0 M BH3•THF (50 mL) with stirring overnight at room temperature. An additional 130 mL 1.0 M BH3•THF was added with stirring for 10 hours. The reaction mixture was quenched by the addition of methanol, stirred 3 hours at room temperature, solvent evaporated, and the product partitioned between aqueous sodium bicarbonate/methylene chloride. The organic layer was dried (sodium sulfate), filtered, and the solvent evaporated. The crude product was purified by flash chromatography over silica gel (ethyl acetate/hexane 1:1) to provide 7.0 g of the title compound.

Workup

  1. stirringwith stirring for 10 hours
  2. customThe reaction mixture was quenched by the addition of methanol
  3. stirringstirred 3 hours at room temperature
  4. customsolvent evaporated
  5. customthe product partitioned between aqueous sodium bicarbonate/methylene chloride
  6. dry with materialThe organic layer was dried (sodium sulfate)
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customThe crude product was purified by flash chromatography over silica gel (ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-c654e088a50640478599a6a665b00561
Source dataset
uspto-grants-2003_02
Patent number
US06518279B2

Reaction notes

Loading…