3-CHLORO-5-FLUOROBENZALDEHYDE

white to yellow low melting solid or clear liquid

Dissolved ferf-butyl (5-bromothiazol-2-yl)carbamate (0.5 g, 2.49 mmol) in tetrahydrofuran (12.4 ml_ ) and cooled to -78 C. Carefully added n-butyllithium (1 .6M in hexanes, 1 .59 ml_, 3.98 mmol) and stirred for 10 minutes, followed by A mixture of Methyl 5-(tert-butyl)isoxazole-3-carboxylate (100mg, 0.5mmol) and NH2NH2 (76mg, 1.5mmol) were dissolved in 5mL EtOH and refluxed for 2h. 3-Chloro-5-fluorobenzaldehyde (402mg, 2.5mmol) was then added and the solution was allowed to stir at rt. for 2h. Then the solution was concentrated and extracted with DCM. After drying over anhydrous Na2SO4, the solution was concentrated and purified with silica gel column (hexane/EtOAc=20/1 to 10/1) to obtain 21 (72mg, 44percent for two steps) as a white solid. 1H NMR (300MHz, CDCl3) delta 9.98 (s, 1H), 8.26 (s, 1H), 7.57 (s, 1H), 7.43 (d, J=7.9Hz, 1H), 7.15 (d, J=6.5Hz, 1H), 6.57 (s, 1H), 1.40 (s, 9H). 13C NMR (75MHz, CDCl3) delta 183.65, 164.37, 157.27, 155.56, 146.48, 136.54, 135.47, 123.77, 118.41, 118.08, 112.89, 112.58, 98.80, 33.06, 28.75.General procedure: The 2-thioxo-4-thiazolidinone (1mmol), benzaldehydes (1 mmol) and NaOH (1.0 mmol) were added to ethanol withtotal volume of 15 mL. The reaction mixture was heated to reflux and stirredfor 2-24 h. After cooling to room temperature, the mixture was concentrated under reduced pressure, neutralized to pH 7.0 with dilute hydrochloric, and then extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated. The resulting residue was recrystallization from ethanol.

Molecular Weight:158.56
XLogP3:2.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:157.9934706
Monoisotopic Mass:157.9934706
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes