Reaktion #54106

Reaktionsgleichung

NH3

iodomethane

2-Benzyl-4-bromo-phenol

2-benzyl-4-bromo-phenol

K2CO3

→

21

Ausbeute 98.0%

2-benzyl-4-bromo-anisole

Ausbeute 98.0%

Lösungsmittel

water

acetone

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture was refluxed for 24 h
2. 2
   Extraktionthe aq. layer was extracted with Et2O
3. 3
   Waschenfractions were washed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Sonstigeevaporated

Vorschrift

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.

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