4-BROMO-2,6-DICHLOROBENZALDEHYDE

In a dry 50 mL r.b. flask under nitrogen atmosphere, oxalyl chloride (0.36 mL, 4.1 mL) was dissolved in dichloromethane (20 mL) and cooled to -78 degrees C. Dimethylsulfoxide (0.66 mL, 9.3 mmol) in dichloromethane (1 mL) was then added dropwise and the reaction was stirred 10 min. at -78 degrees C. A solution of (4-bromo-2, 6-dichlorophenyl)methanol (0.95 g, 3.7 mmol) in dichloromethane (10 mL) was then added dropwise, then the reaction was stirred 30 min. at -78 degrees C. Triethylamine (2.6 mL, 18.5 mmol) was added dropwise and the reaction was stirred 10 min. more at -78 degrees C., then allowed to warm to room temperature and stir 30 min. The reaction mixture was poured into saturated sodium bicarbonate and extracted with dichloromethane (2×). The combined organics were dried over sodium sulfate, concentrated in vacuo, and purified via chromatography (5% ethyl acetate/hexanes) to provide the product, 4-bromo-2, 6-dichlorobenzaldehyde. 1H NMR (400 MHz, CDCl3) delta 7.58 (s, 2H), 10.42 (s, 1H).A solution of 21-1 (830 mg, 3.34 mmol), 4-Bromo-2, 6-dichloroaniline (5, 80 g) was dissolved in acetone (640 mL), and a 48% hydrogen bromide aqueous solution (120 mL) was added, followed by stirring at 0C. A sodium nitrite (32 g) aqueous solution (160 mL) was added dropwise thereto, the mixture was stirred for 30 minutes, and methyl acrylate (200 mL), and water (200 mL) were added, followed by stirring for 1 hour. At room temperature, cuprous oxide (2 g) was added, followed by stirring for 2 hours. The reaction solution was extracted with ethyl acetate, and purified by column chromatography to obtain methyl (E)-3-(4-bromo-2, 6-dichlorophenyl)acrylate (48.5 g). Methyl (E)-3-(4-bromo-2, 6-dichlorophenyl)acrylate (48.5 g) was dissolved in dichloromethane, an ozone gas was introduced at -70C, and ozone oxidization was performed. To the reaction solution was added dimethyl sulfide (40 mL), and this was extracted with ethyl acetate to obtain Triethylphosphonopropionate (26.3 g) was dissolved in THF (150 mL), a THF solution of sodium hydride (6.3 g), and

Molecular Weight:253.90
XLogP3:3.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:251.87443
Monoisotopic Mass:251.87443
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:141
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes