반응 #1074560

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3-Amino-4-fluorobenzoic acid

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title compound

수율 51.1%

3-Amino-4-fluorobenzyl alcohol

수율 51.1%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONtreated with an additional 130 mL of 1.0M borane-tetrahydrofuran complex
2. 2
   workup.STIRRINGstirred 10 hours
3. 3
   기타quenched by the addition of methanol
4. 4
   workup.STIRRINGstirred 3 hours at ambient temperature
5. 5
   농축concentrated
6. 6
   기타partitioned between aqueous sodium bicarbonate/methylene chloride
7. 7
   기타The methylene chloride layer was separated
8. 8
   건조dried (sodium sulfate)
9. 9
   여과filtered
10. 10
    농축concentrated
11. 11
    기타The residue was purified by flash chromatography over silica gel (ethyl acetate:hexanes 1:1)

실험 절차

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.

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