N-bromobutanimide → Methyl 3-(3-bromo-4-cyclopentylmethyloxyphenyl)propionate
Reaction equation
[CH:1]1([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:20]N1C(=O)CCC1=O>C(#N)C>[Br:20][C:13]1[CH:12]=[C:11]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=[CH:9][C:8]=1[O:7][CH2:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of Intermediate 2 (1.31 g) in acetonitrile (50 ml) was added with N-bromosuccinimide (hereinafter abbreviated as “NBS”, 979 mg, KANTO), stirred at room temperature for 2 hours, then warmed to 40° C., and stirred for 3 hours. The reaction mixture was concentrated under reduced pressure, then added with ethyl acetate (200 ml) and washed successively with saturated aqueous ammonium chloride, 5% aqueous sodium sulfite, saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Compound No. A-1, 1.69 g).