Hydrochloric Acid → HCID 135830968, compound
Reaction equation
[Br:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)[S:10][C:6]=2[CH:5]=[C:4]([O:19]C)[CH:3]=1.Cl>B(Br)(Br)Br>[Br:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)[S:10][C:6]=2[CH:5]=[C:4]([OH:19])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Bromo-6-methoxy-2-(4-Methoxy-phenyl)-benzothiazole (200 mg, 0.57 mmol) was suspended in boron tribromide (1M in methylene chloride, 7.5 mL) and stirred at room temp under nitrogen for 3.0 hr. Reaction was poured into aqueous hydrochloric acid (1M) and extracted with ethyl acetate. Ethyl acetate extracts were washed with: 1) hydrochloric acid (1.0M), 2) saturated brine and concentrated in vacuo. Washed solid was further purified by flash chromatography on silica affording the title compound (184 mg, 100%) as a yellow solid. MH+=322