反応 #1892327

反応方程式

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

NaBH4

→

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

収率 43.5%

溶媒

methanol

反応条件

後処理

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

実験手順

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)).

出典