Synthesis
Step 2: Synthesis of 4-thiazol-2-yl-phenol; Boron tribromide (2.00 ml, 15.7 mmol) was added slowly and dropwise to a solution of dichloromethane (25 ml) of the product obtained in step 1 (1.0 g, 5.23 mmol) at -78 °C, keeping the temperature at -78 °C and stirring the reaction for 1 hour. Subsequently, the reaction mixture was warmed to room temperature and stirring was continued for 16 hours. After completion of the reaction, the reaction was quenched by slowly pouring the mixture into ice water. The solid product was collected by filtration and washed with ether to give the final target product 4-thiazol-2-yl-phenol (0.84 g, 84% yield); 1H NMR (400 MHz, CDCl3) δ 7.85 (d, J = 3.2Hz, 1H), 7.79 (d, J = 8.8Hz, 2H), 7.67 (d, J = 3.2Hz, 1H), 7.67 (d, J = 3.2Hz, 1H), 7.67 (d, J = 3.2Hz, 1H), and 6.88 (d, J = 8.8 Hz, 2H); MS (ESI-) m/z 176 ([M-H]-, 100).
References
[1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 6, p. 2299 - 2306
[2] Patent: US2007/66820, 2007, A1. Location in patent: Page/Page column 78
[3] Patent: US2008/33024, 2008, A1. Location in patent: Page/Page column 7; 16
[4] Journal of Medicinal Chemistry, 1986, vol. 29, # 6, p. 1065 - 1080
[5] Journal of the American Chemical Society, 1930, vol. 52, p. 1585
