Thiophosgene → (3-Isothiocyanatophenyl)boronic acid
반응식
[NH2:1][C:2]1[CH:3]=[C:4]([B:8]([OH:10])[OH:9])[CH:5]=[CH:6][CH:7]=1.[C:11](Cl)(Cl)=[S:12]>CC(C)=O.C(Cl)(Cl)Cl>[N:1]([C:2]1[CH:3]=[C:4]([B:8]([OH:10])[OH:9])[CH:5]=[CH:6][CH:7]=1)=[C:11]=[S:12]참가 물질
5
반응 조건
- 온도
- 0 °C
실험 절차
To a cooled (0° C.) solution of 3-aminophenylboronic acid (2.24 g, 0.013 mol) in acetone (5 ml) was added dropwise a solution of thiophosgene (1 ml, 0.013 mol) in chloroform (5 ml) over a period of 0.5 hour. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 12 hours. The solvent was evaporated on a rotary evaporator and the residue was triturated with ether and filtered to remove the triethylamine hydrochloride. The ether solution was evaporated to a brown oil. This was chromatographed on silica gel (30 g) using acetone-chloroform (7:3) as eluent. Fractions containing the product were collected and evaporated to give a light brown solid. This solid was crystallized from ethyl acetate/hexane. M.P. 166°-67° C. Anal. Calcd. for C7H6NSBO2O: C, 46,00; H,3.59; N, 7.67; S, 17.54. Found: C, 46.17; H, 3.48; N, 7.59; S, 17.71.