4-BROMO-2-FLUORO-5-NITROPHENOL

A solution of (9b) (35 g, 113 mmol) in methanol (200 mL) was treated with sodium bicarbonate (19 g, 227 mmol). The reaction mixture was stirred at 60 degree;C for 4 hours. Methanol was evaporated under vacuum. Water (55 mL) was added to the residue and the aqueous layer was acidified to pH5 by addition of a solution of hydrogen chloride 5N. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated in vacuo to afford the product as a yellow solid (25 g, 93percent). MS (+ve ion electrospray) m/z 237 (MH+).c) 4-bromo-2-fluoro-5-nitrophenol; A solution of 4-bromo-2-fluoro-5-nitrophenyl ethyl carbonate (35 g, 113 mmole) in MeOH (200 mL) was treated with sodium bicarbonate (19 g, 227 mmole). The reaction mixture was stirred at 60 C for 4 hours. The methanol was evaporated under vacuum. Water (55 mL) was added to the residue and the aqueous layer was acidified to pH=5 by addition of a solution of 6N hydrogen chloride. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated under vacuum to afford the title compound (25g, 93percent) as a yellow solid. LC- MS (ES) (M+H)+ m/z = 237.

Molecular Weight:235.99
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:234.92803
Monoisotopic Mass:234.92803
Topological Polar Surface Area:66
Heavy Atom Count:12
Complexity:186
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes