반응 #54106

반응 방정식

NH3

iodomethane

2-Benzyl-4-bromo-phenol

2-benzyl-4-bromo-phenol

K2CO3

→

21

수율 98.0%

2-benzyl-4-bromo-anisole

수율 98.0%

용매

water

acetone

CH2Cl2

반응 조건

후처리

1. 1
   온도the resulting mixture was refluxed for 24 h
2. 2
   추출the aq. layer was extracted with Et2O
3. 3
   세척fractions were washed with brine
4. 4
   건조dried over Na2SO4
5. 5
   기타evaporated

실험 절차

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.

출처