1-CHLORO-5-FLUORO-2-METHOXY-4-NITROBENZENE

To a solution of 2-chloro-4-fluoro-5-nitrophenol (5.Og, 26.lmmol) in acetone (lOOmL) were added K2003 (18 g, l3lmmol) and methyl iodide (8.OmL, 131 mmol) at rt. The reaction mixture was stirred at rt for 2h. TLC showed the reaction to be complete. The reaction mixture was evaporated under reduced pressure, diluted with H20 (lOOmL) and extracted with EtOAc (3xlOOmL). The organic layer was washed with H20 (lOOmL), brine (lOOmL), dried (Na2SO4), filtered and concentrated under reduced pressure to give 1 -chloro-5-fluoro-2-methoxy-4-nitrobenzene as a yellow solid. Yield: 5.0 g (93percent); 1H NMR (400 MHz, DMSO-d6): 7.94-7.97 (m, 1H), 7.81-7.83 (m, 1H) 3.95 (5, 3H).To a mixture of a (6.0 g, 29.1 mmol, 1.0 eq) and CS2CO3 (29.0 g, 87.4 mmol 0 eq) in DMF (100 mL) was added isopropanol (5.3 g, 87.4 mmol, 3.0 eq). The mixture was stirred at room temperature overnight. Water (300 mL) was added and the mixture was extracted with EtOAc (100 mL x 3). The combined organics were washed with brine and concentrated to afford b (7.1 g, 99percent) as brown oil

Molecular Weight:205.57
XLogP3:2.5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:204.9941989
Monoisotopic Mass:204.9941989
Topological Polar Surface Area:55
Heavy Atom Count:13
Complexity:199
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes