2-Aminophenol → HCID 23366240, compound

Participants

Reaction Steps

To a stirred solution of 1.0 g (9.16 mmol) of o-aminophenol in 10 mL of tetrahydrofuran was added 3.57 mL (2.59 g; 25.6 mmol) of triethylamine and 3.46 g (22.9 mmol) of t-butyldimethylsilyl chloride. The reaction mixture was stirred for 15 hours at room temperature, filtered and concentrated in vacuo. The residue was dissolved in 10 mL of toluene and this solution was cooled to -15° C. The solution was treated with 1.4 mL (1.02 g; 10.0 mmol) of triethylamine, followed by the dropwise addition of 4.75 mL (9.17 mmol) of a 1.93M solution of phosgene in toluene. After the addition was complete, the reaction mixture was allowed to warm up to room temperature and stirred at that temperature for 1 hour. The mixture was filtered and the filtrate was concentrated in vacuo to give a pink oil. IR (neat) 2251 cm-1 ; 1H NMR (CDCl3) δ7.060 (dt, J=8.4, 2.0 Hz, 1H, ArH), 7.018 (dd, J=7.6, 2.0 Hz, 1H, ArH), 6.950-6.850 (m, with d at 6.894, J=7.6 Hz, 2H, ArH), 1.08 (s, 9H, CCH3), 0.350 (s, 6H, SiCH3); MS (EI) m/z=192 (100%), 249 (M+).

Provenance & Evidence