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

HRID 987378Notes

Reaction equation

HRID 987378 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]>O1CCCC1>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[CH2:5][OH:6]

Participants

3

Reactant 1

HCID 753963-Amino-4-fluorobenzoic acid

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 tetrahydrofuran at 0° C. was treated with 1.0M borane-tetrahydrofuran complex (50 mL), stirred overnight at ambient temperature, treated with an additional 130 mL of 1.0M borane-tetrahydrofuran complex, stirred 10 hours, quenched by the addition of methanol, stirred 3 hours at ambient temperature, concentrated and partitioned between aqueous sodium bicarbonate/methylene chloride. The methylene chloride layer was separated, dried (sodium sulfate), filtered, and concentrated. The residue was purified by flash chromatography over silica gel (ethyl acetate:hexanes 1:1) to provide 7.0 g of the title compound.

Workup

  1. additiontreated with an additional 130 mL of 1.0M borane-tetrahydrofuran complex
  2. stirringstirred 10 hours
  3. customquenched by the addition of methanol
  4. stirringstirred 3 hours at ambient temperature
  5. concentrationconcentrated
  6. custompartitioned between aqueous sodium bicarbonate/methylene chloride
  7. customThe methylene chloride layer was separated
  8. dry with materialdried (sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by flash chromatography over silica gel (ethyl acetate:hexanes 1:1)

Sources & evidence

ORD record
ord-f37807fbd77147aaa083f9af139e2112
Source dataset
uspto-grants-2003_10
Patent number
US06632418B2

Reaction notes

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