반응 #1145858

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BH3•THF

3-Amino-4-fluorobenzoic acid

BH3•THF

→

title compound

수율 51.1%

3-Amino-4-fluorobenzyl alcohol

수율 51.1%

용매

THF

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후처리

1. 1
   workup.STIRRINGwith stirring for 10 hours
2. 2
   기타The reaction mixture was quenched by the addition of methanol
3. 3
   workup.STIRRINGstirred 3 hours at room temperature
4. 4
   기타solvent evaporated
5. 5
   기타the product partitioned between aqueous sodium bicarbonate/methylene chloride
6. 6
   건조The organic layer was dried (sodium sulfate)
7. 7
   여과filtered
8. 8
   기타the solvent evaporated
9. 9
   기타The crude product was purified by flash chromatography over silica gel (ethyl acetate/hexane 1:1)

실험 절차

3-Amino-4-fluorobenzoic acid (15 g, 97 mmol) in THF at 0° C. was treated with 1.0 M BH3•THF (50 mL) with stirring overnight at room temperature. An additional 130 mL 1.0 M BH3•THF was added with stirring for 10 hours. The reaction mixture was quenched by the addition of methanol, stirred 3 hours at room temperature, solvent evaporated, and the product partitioned between aqueous sodium bicarbonate/methylene chloride. The organic layer was dried (sodium sulfate), filtered, and the solvent evaporated. The crude product was purified by flash chromatography over silica gel (ethyl acetate/hexane 1:1) to provide 7.0 g of the title compound.

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