Boron tribromide → HCID 59557707, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[O:18]C.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[OH:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-bromo-4-chloro-5-(4-ethylbenzyl)-2-methoxybenzene (AS) (5.1 g, 15 mmol) in anhydrous CH2Cl2 (15 mL), the solution of BBr3 in CH2Cl2 (1M, 20 mL) was added dropwise at −5° C. After BBr3 was added, the reaction mixture was allowed to warm to room temperature and stirred for 2 h, after which TLC showed the reaction was complete. The reaction was quenched with saturated NaHCO3. The organic phase was separated and washed with water and brine. After drying with anhydrous Na2SO4, the organic portion was filtered and concentrated to give AT as an oil (4.49 g, yield 92%). 1H-NMR (CDCl3, 300 MHz) δ 7.22 (s, 1H), 7.13 (m, 4H), 7.07 (s, 1H), 5.42 (s, 1H), 3.99 (s, 2H), 2.54 (q, J=7.5 Hz, 2H), 1.23 (t, J=7.5 Hz, 3H).