反应详情

温度

115 °C

Methyl 4-nitro-2-bromobenzoate (11.40 g, 43.85 mmol) was dissolved in 100 mL of DMF. Air was removed and the system was flushed with nitrogen. To this solution was added Pd(PPh3)4 (1.63 g, 3.1% eq). The pale yellow solution was stirred for 15 min until the color changed to deep brown. 2-Tolylboronic acid (6.6 g, 48.5 mmol) was added followed by anhydrous K2CO3 (18.2 g, 3.0 eq). The mixture was heated at 115° C. for 18 hr and then cooled down. This mixture was diluted with 100 mL of ether and 50 mL of water. The aqueous solution was extracted with ether. The ether solution was washed with 1N hydrochloric acid and then dried and evaporated. The residue was purified by flash column chromatography (10:1=hexane/ethyl acetate) to give a pale yellow oil which slowly solidifies (11.53 g, 97% yield). 1H NMR (CDCl3) δ 8.28 (d, J=8.7 Hz, 1H), 8.06-8.13 (s and d, 2H), 7.22-7.34 (m, 3H), 7.07 (d, J=7.3 Hz, 1H), 3.66 (s, 3H), 2.10 (s, 3H), 13C NMR (CDCl3) δ 165.7, 148.6, 143.5, 138.5, 135.9, 134.7, 130.5, 129.3, 127.9, 127.7, 125.1, 121.5, 51.8, 19.3; HRMS (EI) calcd for Cl5H13O4N 271.0844, obsd 271.0842.

1. customAir was removed
2. customthe system was flushed with nitrogen
3. additionTo this solution was added Pd(PPh3)4 (1.63 g, 3.1% eq)
4. temperaturecooled down
5. extractionThe aqueous solution was extracted with ether
6. washThe ether solution was washed with 1N hydrochloric acid
7. customdried
8. customevaporated
9. customThe residue was purified by flash column chromatography (10:1=hexane/ethyl acetate)
10. customto give a pale yellow oil which