Benzyl Bromide → Ethyl 2-[4-benzyloxy-2-nitronaphthalen-1-yl]acetate

Anhydrous K2CO3 (0.50 g, 3.68 mmol) was added to a solution of ethyl 2-[4-hydroxy-2-nitronaphthalen-1-yl]acetate (0.42 g, 1.53 mmol) and benzyl bromide (0.44 mL, 3.68 mmol) in acetone (4 mL) at room temperature, and the mixture was stirred overnight. The reaction mixture was filtered, and the filtrate was concentrated. The residue was diluted with AcOEt (50 mL), and to the mixture was added N-methypiperazine (3 mL) to remove any excess benzyl bromide. The mixture was washed with water (10 mL), 1 M HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and saturated aqueous NaCl (10 mL), and then dried (Na2SO4) and evaporated to yield ethyl 2-[4-benzyloxy-2-nitronaphthalen-1-yl]acetate (0.35 g, 63%) as a yellow solid. Mp 128-130° C.; 1H NMR (CDCl3, 500 MHz) δ 8.44 (dd, 0.5, 8.0, 1H), 8.10 (d, 8.5, 1H), 7.71 (t, 7.0, 1H), 7.66 (t, 7.0, 1H), 7.54 (d, 7.0, 2H), 7.46 (t, 7.5, 2H), 7.43 (s, 1H), 7.40 (t, 7.0, 1H), 5.32 (s, 2H), 4.33 (s, 2H), 4.21 (q, 7.0, 2H), 1.27 (t, 7.0, 3H); EIMS m/z 365 (M+); IR (neat) νmax 2980, 1725, 1592, 1524, 1512, 1469, 1451, 1426, 1371, 1331, 1252, 1202, 1159, 1111, 1022, 842, 770, 756, 724, 690 cm−1.

1. filtrationThe reaction mixture was filtered
2. concentrationthe filtrate was concentrated
3. additionThe residue was diluted with AcOEt (50 mL)
4. additionto the mixture was added N-methypiperazine (3 mL)
5. customto remove any excess benzyl bromide
6. washThe mixture was washed with water (10 mL), 1 M HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and saturated aqueous NaCl (10 mL)
7. dry with materialdried (Na2SO4)
8. customevaporated

ORD record

ord-1f38b9929a1c4bbc98e7f590a87fb850

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06660742B2