Thiophosgene → (3-Isothiocyanatophenyl)boronic acid

Temperature

0 °C

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.

1. customThe solvent was evaporated on a rotary evaporator
2. customthe residue was triturated with ether
3. filtrationfiltered
4. customto remove the triethylamine hydrochloride
5. customThe ether solution was evaporated to a brown oil
6. customThis was chromatographed on silica gel (30 g)
7. additionFractions containing the product
8. customwere collected
9. customevaporated
10. customto give a light brown solid
11. customThis solid was crystallized from ethyl acetate/hexane

ORD record

ord-73d56fd6c6c649b0b3838bf6c0d7e9a6

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05183653