Chlorosuccinimide → 5-Chloro-2-ethoxybenzoic acid
Reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Cl:13]N1C(=O)CCC1=O>C(#N)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-ethoxybenzoic acid (4.4 g, 26.6 mmol) in 80 mL of acetonitrile at 0° C. was added N-chlorosuccinimide (3.7 g, 28 mmol) in 20 mL of acetonitrile dropwise over 30 minutes. The reaction mixture was warmed to ambient temperature and the mixture was allowed to stir for 70 hours. The mixture was quenched with 20 mL of H2O and the layers were separated. The aqueous layer was extracted with three 15 mL portions of CH2Cl2 and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via recrystallization with ether and hexanes afforded the title compound. MS (DCI/NH3) m/z 201 (M+H)+, 218 (M+NH4)+.