反应详情

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 room 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 room 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/hexane 1:1) to provide 7.0 g of the title compound.

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 room 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/hexane 1:1)