Dichloromethane → HCID 21112933, compound
Reaction equation
C([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22]C)[CH:6]=1)C.ClCCl>B(Br)(Br)Br>[OH:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:12]1[CH2:13][CH2:14][CH2:15][C:11]=1[C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([OH:24])=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-[2-(2-Methoxy-phenyl)-cyclopent-1-enyl]-benzoic acid ethyl ester (610 mg, 1.89 mmol) was dissolved in 1M boron tribromide in dichloromethane solution (18.9 ml, 18.9 mmol) and left at room temperature for 18 hours. The resulting solution was poured onto ice and extracted with dichloromethane. The organic extract was dried (MgSO4), evaporated to dryness and purified by chromatography using biotage with iso-hexane containing a gradient of ethyl acetate (20–40%) to yield the title compound as a light brown solid. (186 mg, 35%).