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

HRID 1837058Notes

Reaction equation

HRID 1837058 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]([CH2:5][OH:6])[CH:8]=[CH:9][C:10]=1[F:11]

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 1.0 M borane-tetrahydrofuran complex (50 mL). After stirring overnight at ambient temperature, the mixture was treated with an additional 130 mL of 1.0 M borane-tetrahydrofuran complex. After stirring for 10 hours, the mixture was 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 dried (sodium sulfate), filtered and concentrated. The residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 1:1) to provide 7.0 g of the title compound.

Workup

  1. additionthe mixture was treated with an additional 130 mL of 1.0 M borane-tetrahydrofuran complex
  2. stirringAfter stirring for 10 hours
  3. customthe mixture was quenched by the addition of methanol
  4. stirringstirred 3 hours at ambient temperature
  5. concentrationconcentrated
  6. custompartitioned between aqueous sodium bicarbonate/methylene chloride
  7. dry with materialThe methylene chloride layer was dried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-835c0f2019714314a849885884e6a089
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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