反応 #661301

反応方程式

Copper(I) cyanide

2,5-dibromo-3-methylpyridine

2,5-Dibromo-3-methylpyridine

water

→

50

収率 74.0%

5-Bromo-3-methylpicolinonitrile

収率 74.0%

溶媒

DMF

反応条件

後処理

1. 1
   温度the mixture was heated
2. 2
   温度at reflux for 2 h
3. 3
   抽出the products were extracted with ethyl acetate (3×300 mL)
4. 4
   洗浄The combined extracts were washed with water (3×300 mL), brine (300 mL)
5. 5
   乾燥dried with sodium sulfate
6. 6
   その他evaporated to dryness
7. 7
   洗浄eluting with chloroform

実験手順

Copper(I) cyanide (21 g, 0.24 mol) was added to a solution of 2,5-dibromo-3-methylpyridine (49, 60 g, 0.24 mol) in dry DMF (200 mL), and the mixture was heated at reflux for 2 h. After cooling to room temperature, water (1500 mL) was added to the mixture and the products were extracted with ethyl acetate (3×300 mL). The combined extracts were washed with water (3×300 mL), brine (300 mL), dried with sodium sulfate and evaporated to dryness. The brown oily residue was subjected to flash column chromatography (silica gel), eluting with chloroform, to yield 50 as a white solid (35 g, 74%): mp 86-88° C. 1H NMR (300 MHz, CDCl3) δ 8.55 (d, J=1.8 Hz, 1H), 7.84 (d, J=1.5 Hz, 1H), 2.53 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 149.75, 140.68, 139.95, 132.25, 124.61, 115.90, 18.59; EIMS m/z 196/198 (M+); CIMS 197/199 (MH+). The 1H NMR spectrum is consistent with previously published data (Bioorg. Med. Chem. 1999, 7, 1845-1855).

出典