HCID 67126235, compound → 6-Chloro-7-fluoro-3-methylnaphthalen-1-ol
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([CH3:17])=[CH:11][C:12]([O:14]CC)=O)[CH:5]=[CH:6][C:7]=1[F:8]>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[F:8])[C:12]([OH:14])=[CH:11][C:10]([CH3:17])=[CH:9]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of ethyl 4-(3-chloro-4-fluorophenyl)-3-methylbut-2-enoate (9.7 g, 37.8 mmol) in concentrated sulfuric acid (40 mL) was stirred at 50° C. overnight. The reaction mixture was poured onto ice and diluted with water and extracted with ethyl acetate. The organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a pale yellow solid (1.57 g). 1H-NMR: 400 MHz, (CDCl3) δ: 7.83 (d, J=10.4 Hz, 1H), 7.75 (d, J=7.2 Hz, 1H), 7.11 (s, 1H), 6.67 (s, 1H), 2.42 (s, 3H).