反応 #54106

反応方程式

NH3

iodomethane

2-Benzyl-4-bromo-phenol

2-benzyl-4-bromo-phenol

K2CO3

→

21

収率 98.0%

2-benzyl-4-bromo-anisole

収率 98.0%

溶媒

water

acetone

CH2Cl2

反応条件

後処理

1. 1
   温度the resulting mixture was refluxed for 24 h
2. 2
   抽出the aq. layer was extracted with Et2O
3. 3
   洗浄fractions were washed with brine
4. 4
   乾燥dried over Na2SO4
5. 5
   その他evaporated

実験手順

9.48 ml (152 mmol, 10 eqv) iodomethane was added to a suspension of 4.00 g (15.2 mmol) 2-Benzyl-4-bromo-phenol (20) and 10.50 g (76 mmol, 5 eqv) K2CO3 in 70 ml acetone and the resulting mixture was refluxed for 24 h. After adding water and aq. NH3-solution, the aq. layer was extracted with Et2O. The comb. org. fractions were washed with brine, dried over Na2SO4 and evaporated. Column chromatography (CH2Cl2) yielded 4.11 g (14.8 mmol, 98%) 21 as a colorless liquid: Rf (CH2Cl2) 0.77; 1H NMR (400 MHz, CDCl3) δ 3.79 (s, 3H), 3.92 (s, 2H), 6.72 (d, 1H, J=8.59 Hz), 7.18 (m, 4H), 7.27 (m, 3H); LRMS (EI) m/z 279 (17), 278 (95), 277 (18), 276 (96), 263 (14), 261 (17), 198 (18), 197 (65), 182 (34), 181 (31), 166 (20), 165 (56), 154 (19), 153 (24), 152 (29), 92 (11), 91 (100), 77 (13), 76 (16), 63 (13); HRMS (EI) Calcd. for C14H13BrO: 276.014976. Found: 276.014234.

出典