1-(Benzyloxy)-2-methyl-3-nitrobenzene

41.5 g (300 mmol) of potassium carbonate and 200 ml of N, N-dimethylformamide were added to 30.6 g (200 mmol) of 2-methyl-3-nitrophenol. A mixture of 2-methyl-3-nitrophenol (672 mg, 4.4 mmol), cesium carbonate (2.1 g, 6.44 mmol), and benzyl bromide (751 mg, 4.4 mmol) in DMF (6 mL) was stirred at room temperature for 3 h. The reaction mixture was poured into ice water. The light yellow precipitation was filtered off, washed several times with water, and dried, to provide 1-nitro-2-methyl-3-[(phenylmethyl)oxy]benzene (930 mg, 87percent yield). (at)HNMR (400 MHz, d4-methanol): 8 7.47 (d, 1H), 7.45 (s, 1H), 7.40 (s, 1H), 7.39 (d, 1H), 7.37 (d, 1H), 7.34 (m, 1H), 7.32 (s, 1H), 7.29 (d, 1H), 4.90 (s, 2H), 2.35 (s, 3H).To a 500-mL 3-necked round-bottom flask was placed a solution of 2-methyl-3-nitrophenol (10 g, 65.30 mmol) and K2C03 (13 g, 94.06 mmol) in CH3CN (100 mL) then BnBr (13 g, 76.01 mmol) was added. The reaction was stirred at 90°C for 2 h, cooled to rt, filtered, and concentrated under reduced pressure. Thecrude product was purified by column chromatography eluting with EtOAc/petroleum ether (1:9) affording 8.6 g of the title compound as a yellow oil.(Referential Example 22)

Molecular Weight:243.26
XLogP3:4.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:243.08954328
Monoisotopic Mass:243.08954328
Topological Polar Surface Area:55
Heavy Atom Count:18
Complexity:271
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes