Methyl 3-bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzoate → Methyl 3-bromo-5-(3-methoxypropyl)-4-methylbenzoate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10](/[CH:13]=[CH:14]/[CH2:15][O:16][CH3:17])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6]>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CC=CCCC=C1.C1C=CN=CC=1.F[P-](F)(F)(F)(F)F.[Ir].ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:13][CH2:14][CH2:15][O:16][CH3:17])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a dichloromethane (0.2 M) solution of methyl 3-bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzoate (1 eq.) from the previous step was added Crabtree's catalyst (0.01 eq.). The resulting orange red solution was bubbled with hydrogen for 10 min to activate the catalyst and then stirred at RT under a static balloon atmosphere of hydrogen for 3 h. Finally, removal of the volatiles in vacuo afforded the crude title compound as a yellow oil.