反应详情

温度

0 °C

Nitrobenzene (45 ml) was cooled in an ice-bath and treated portionwise with aluminum chloride (13.5 g, 101 mmol, 1.15 eq.) and followed by 4-iodobenzoic acid chloride (25 g, 94 mmol, 1.07 eq.) in nitrobenzene (25 ml) at a maximum of 10° C. The mixture was stirred at 0° C. for 10 minutes, where upon anisole (9.5 g, 88 mmol, 1 eq.) was added dropwise in such a manner that the temperature didn't excess 10° C. The solution then was left to warm to room temperature overnight. The yellow suspension was poured into ice-water (750 ml). The precipitate was collected by filtration and washed with water and then dissolved in dichloromethane (2 L), which was washed NaHCO3 (aq.) (150 ml×2), dried over MgSO4. Evaporation of solvent under reduced pressure to provide the title product in (26.7 g, 90%), 1H NMR (400 MHz, CDCl3) δ 3.89 (s, 3H), 6.96 (d, J=8.4 Hz, 2H), 7.48 (d, J=8.0 Hz, 2H), 7.79 (d, J=8.4 Hz, 2H), 7.84 (d, J=8.0 Hz, 2H);

1. customdidn't excess 10° C
2. waitThe solution then was left
3. temperatureto warm to room temperature overnight
4. filtrationThe precipitate was collected by filtration
5. washwashed with water
6. dissolutiondissolved in dichloromethane (2 L)
7. washwhich was washed NaHCO3 (aq.) (150 ml×2)
8. dry with materialdried over MgSO4
9. customEvaporation of solvent under reduced pressure