反応 #45332

反応方程式

H2O

3-nitro-5-(trifluoromethyl)benzoic acid

borane THF

→

[3-nitro-5-(trifluoromethyl)phenyl]methanol

溶媒

THF

THF

反応条件

後処理

1. 1
   抽出The resultant mixture was extracted with EtOAc (100 mL)
2. 2
   洗浄the organic layer was washed with brine (50 mL)
3. 3
   乾燥dried over Na2SO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他Purification by flash chromatography with 50% EtOAc/hexanes

実験手順

To a solution of 3-nitro-5-(trifluoromethyl)benzoic acid (2.0 g, 8.5 mmol) in THF (100 mL) was added borane-THF (17 mL of a 1 M solution in THF, 17 mmol). The reaction was stirred at 60° C. for 24 hours and then poured into H2O (50 mL). The resultant mixture was extracted with EtOAc (100 mL) and the organic layer was washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 50% EtOAc/hexanes afforded [3-nitro-5-(trifluoromethyl)phenyl]methanol. Rf=0.35 (75% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) 8.44 (s, 1H), 8.40 (s, 1H), 7.98 (s, 1H), 4.91 (s, 2H), 2.07 (bs, 1H).

出典