* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
3-(2-chloro-4-fluorophenyl)propionyl chloride[ No CAS ]
[ 166250-01-7 ]
Yield
Reaction Conditions
Operation in experiment
aluminium chloride; In dichloromethane;
A solution of the 3-(2-chloro-4-fluorophenyl) propionyl chloride in dichloromethane (100 ml) was added dropwise to a mixture of aluminium chloride (17.3 g, 0.13 mol, Aldrich) in dichloromethane (100 ml) at room temperature. After the addition was completed, the mixture was refluxed for 2.5 h. The reaction mixture was poured into ice water (1.5 L). The two phases were separated and the dichloromethane phase was washed with 0.1N aqueous sodium hydroxide, dried (Na2 SO4), and concentrated to give crude 4-chloro-6-fluoro-1-indanone. Chromatography on silica gel with hexanes:dichloromethane (1:1) as eluent gave 11.1 g (55%) of 4-chloro-6-fluoro-1-indanone as a white solid: mp 94-96 C.
With n-butyllithium; ammonium chloride; diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; water; ethyl acetate;
d) Preparation of Ethyl 2-(4-Chloro-6-fluoro-1-hydroxy-1-indanyl)acetate Ethyl acetate (5.9 g, 0.07 mol) was added dropwise to a stirred, chilled (dry ice-acetone bath) solution of lithium diisopropylamide (prepared by dropwise addition of a 2.5M solution of n-butyllithium (26.8 ml, 0.07 mol) in hexane to a chilled (dry ice-acetone bath) solution of diisopropylamine (6.8 g, 0.07 mol) in tetrahydrofuran (35 ml)). After 30 min, a solution of <strong>[166250-01-7]4-chloro-6-fluoro-1-indanone</strong> (12.4 g, 0.07 mol) in tetrahydrofuran (100 ml) was added dropwise and the mixture was stirred for 1 h (dry ice-acetone bath). A solution of ammonium chloride (10.6 g, 0.20 mol) in water (80 ml) was added and the mixture was allowed to come to ambient temperature. The aqueous phase was separated and extracted with diethyl ether. The combined organic phase was dried (sodium sulphate), filtered and concentrated in vacuo to give 19.5 g of crude ethyl 2-(4-chloro-6-fluoro-1-hydroxy-1-indanyl)acetate. Chromatography on silica gel with hexanes:ethyl acetate (8:2) as eluent gave 15.2 g (83%) of a yellow oil; NMR (DMSO-d6): a 7.13-7.28 (m, 2H), 5.55 (s, 1H), 3.98 (m, 2H), 2.79 (2m's, 4H), 2.50 (m, 1H), 2.11 (m, 1H). 1.08 (t, 3H).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
