Boron tribromide → HCID 58415368, compound
Reaction equation
B(Br)(Br)Br.[I:5][C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][C:18]=1[O:19]C)[CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1>C(Cl)Cl>[I:5][C:6]1[CH:7]=[C:8]([CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:16]=[CH:17][C:18]=1[OH:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Boron tribromide (11.1 mL, 11.1 mmol, 1M in DCM) was added to a solution of 3-(3-iodo-4-methoxybenzyl)pyridine (720 mg, 2.21 mmol) in DCM (3 mL) at 0° C., and the mixture was stirred for 1 h. The mixture was quenched by the careful addition of water, the layers were separated, and the organic layer was washed with water three times. The combined organic extracts were dried over MgSO4, concentrated in vacuo, and purified by column chromatography to give 2-iodo-4-(pyridin-3-ylmethyl)phenol as a yellow oil. MS (ESI) m/z: Calculated: 311.0; Observed: 312.3 (M++1).