1-Bromo-3-chloropropane → Methyl 4-(3-chloropropoxy)benzoate
Reaction equation
C(N([CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)CC)C.[C:18]([O-])([O-])=O.[Cs+].[Cs+].BrCC[CH2:27][Cl:28]>CN(C=O)C>[Cl:28][CH2:27][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:15][CH3:18])=[O:14])=[CH:11][CH:10]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of Methyl 4-hydroxy benzoic acid (23-2) (Aldrich) (4.56 g, 30 mmol) in DMF (100 mL) was treated with Cs2CO3 (14.67 g, 45 mmol) at room temperature. After 0.5 hours, 3-bromo-1-chloropropane (5.94 mL, 60 mmol) was added and the solution was stirred for 4 hours. The reaction mixture was filtered and concentrated to give 27-1 as a white solid. Rf (10% EtOAc/hexanes) 0.36.