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

HRID 1386051Notes

Reaction equation

HRID 1386051 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), stirred overnight at room temperature, treated with an additional 130 mL 1.0 M BH3.THF, stirred 10 hours, quenched by the addition of methanol, stirred 3 hours at room temperature, solvent evaporated, the product partitioned between aqueous sodium bicarbonate/methylene chloride, the organic layer dried (sodium sulfate), filtered and solvent evaporated. The 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. stirringstirred 10 hours
  2. customquenched 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 dried (sodium sulfate)
  7. filtrationfiltered
  8. customsolvent evaporated
  9. customThe product was purified by flash chromatography over silica gel (ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-727e07fa07db4bd79b45d999a49a16e4
Source dataset
uspto-grants-2001_07
Patent number
US06265417B1

Reaction notes

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