2-Bromo-1-isopropoxy-3-nitrobenzene → HCID 18687703, compound

Participants

Reaction Conditions

Reaction Steps

Potassium tert-butoxide (360 mg, 3.2 mmol) was added to a stirred, degassed, solution of 3-fluoro-2-mercaptophenol (390 mg, 2.7 mmol) and 2-bromo-3-isopropoxy-nitrobenzene in 20 mL anhydrous DMF and the resulting burgandy-colored reaction heated at 80° C. under N2 overnight (17 h). After cooling to room temperature 10% aqueous HCL (100 ml) was added and the reaction mixture washed with EtOAc (2×75 ml). The combined organics were rinsed with water (2×200 ml), and brine (200 ml), dried (Na2SO4), and concentrated in vacuo to a viscous orange-brown oil. Purification by column chromatography afforded 390 mg (45% from O-2-(4-methoxybenzyl)thio-3-fluorophenyl N,N-diethylcarbamate) of 3-fluoro-2-((4-isopropoxy-2-nitrophenyl)thio)phenol as a yellow solid along with 60 mg (8%) of 1-fluoro-7-isopropoxyphenoxathiin.

Provenance & Evidence