Sodium Hydroxide → 1-Bromo-3-methyl-5-nitro-2-vinylbenzene

Participants

Reaction Conditions

Reaction Steps

The reaction mixture of 2-Bromo-6-methyl-4-nitrophenyl trifluoromethanesulfonate (10.0 g, 27.5 mmol), vinyl-tri-n-butyltin (8.7 g, 27.5 mmol), LiCl (1.4 g, 33.0 mmol), Pd(dppf)Cl2 (673 mg, 0.92 mmol) and DMF (50 mL) was stirred at 70° C. for 3 h under N2. Then 2 N aq. NaOH (30 mL) was added and stirred at 70° C. for 10 min. The reaction mixture was cooled down, washed with saturated aqueous NaHCO3 (100 mL), and extracted with EtOAc (3×50 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered, concentrated in vacuo, and purified by silica gel column (Petroleum Ether→Petroleum Ether:EtOAc (50:1)) to afford 1-Bromo-3-methyl-5-nitro-2-vinylbenzene (2.01 g, 30%) as yellow oil. 1H-NMR: 400 MHz, (CDCl3) δ: 8.29 (d, J=2.0 Hz, 1H), 8.02 (s, 1H), 6.67 (dd, J=17.6, 11.6 Hz, 1H), δ 5.75 (d, J=11.6 Hz, 1H), δ 5.49 (d, J=18.0 Hz, 1H), δ 2.48 (s, 3H).

Provenance & Evidence