Boron tribromide → HCID 23296008, compound
Reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[C:8]([CH2:14][CH3:15])[CH:7]=1)=[O:5].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:14][CH3:15])[CH:7]=1)=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
At -78° C., to a stirred solution of 4-(2-chlorobenzoyl)-2-ethylanisole (18 g, 65.5 mmol) in CH2Cl2 (295 mL) was added boron tribromide (12.4 mL, 0.131 mol). After the addition was complete, the reaction was allowed to warm to ambient temperature and stirred for 48 h. The reaction was slowly poured into crushed ice (200 g) and extracted with CH2Cl2. The organic extracts were washed with sat. aq. KH2PO4 (1×) and extracted with 2.5N NaOH. The aqueous extracts were washed with CH2Cl2 (1×), acidified with 2N HCl and extracted with CH2Cl2, dried (Na2SO4) and concentrated to give 14.48 g (85%) of the title compound. 1H NMR: consistent. mass spectrum (+ESI) m/z 261 (M+H). Anal. Calcd. for C15H13ClO2.0.2H2O: C, 68.16; H, 5.11; N, 0.00. Found: C, 68.18; H, 5.15; N, 0.00.