反应 #1892327

反应方程式

1-(benzyloxy)-4-fluoro-5-nitro-2-(trifluoromethyl)benzene

NaBH4

→

5-(benzyloxy)-2-fluoro-4-(trifluoromethyl)aniline

收率 43.5%

溶剂

methanol

反应条件

后处理

1. 1
   其他The reaction mixture was quenched with NaHCO3
2. 2
   workup.ADDITIONdiluted with EtOAc
3. 3
   过滤The reaction mixture was then filtered through a plug of celite
4. 4
   其他the layers separated
5. 5
   萃取the aqueous layer was extracted with EtOAc
6. 6
   干燥The combined organic layer was dried over Na2SO4
7. 7
   过滤filtered
8. 8
   浓缩concentrated
9. 9
   其他The residue was then purified by silica gel column chromatography

实验过程

To a solution of 1-(benzyloxy)-4-fluoro-5-nitro-2-(trifluoromethyl)benzene (382 mg, 1.21 mmol) and NiCl2 (314 mg, 2.42 mmol) in methanol (40 mL) was added NaBH4 (50 mg, 1.32 mmol) portionwise at 0° C. The reaction turned black after 20 minutes. The reaction mixture was quenched with NaHCO3 and diluted with EtOAc. The reaction mixture was then filtered through a plug of celite, the layers separated and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4, filtered and concentrated. The residue was then purified by silica gel column chromatography using 15% EtOAc/hexane gradient to give 5-(benzyloxy)-2-fluoro-4-(trifluoromethyl)aniline (150 mg, 43%). LC/MS: m/z 286.1 (M+H)+ at 1.89 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

来源