反应详情

To a stirred solution of benzyl alcohol (3.86 g, 20 mmol) in DMA (30 ml), NaH (60% dispersion in oil, 0.80 g, 20 mmol) was drop wisely added. After one hour, 1-bromo-3,5-difluorobenzen (3.86 g, 20 mmol) was added at such a rate to maintain the temperature no more than 40° C. The mixture was stirred at ambient temperature overnight. The reaction was quenched by water and extracted with EtOAc. It was purified via flash chromatography and gave the product (4.17 g, 74%) as colorless oil. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.41-7.43 (m, 5H), 6.94 (m, 1H), 6.86 (dt, 1H), 6.63 (dt, 1H), 5.02 (s, 2H); 13C NMR (CDCl3, 75 MHz) δ 165.20, 161.89, 160.72, 160.56, 136.01, 128.94, 128.57, 127.77, 127.73, 122.99, 122.83, 114.58, 114.53, 112.18, 111.84, 102.29, 101.96, 70.76; 19F NMR (CDCl3, 282 MHz) δ −31129.40 (t, J=2583.12 Hz).

1. additionwisely added
2. temperatureto maintain the temperature no more than 40° C
3. customThe reaction was quenched by water
4. extractionextracted with EtOAc
5. customIt was purified via flash chromatography