5-(4-CHLOROPHENYL)-2-FURALDEHYDE

Pale brown needles

General procedure: The compounds 5-arylfuran-2-carbaldehydes (1-9) were synthesized and characterized according to the reported method[3, 13].In a 250 mL round bottom three-necked flask was added O.Olmol 4-chloroaniline and a small amount of ethanol, OmL (0.035 mol) was added dropwise with stirring under ice-cooling.Dissolve 0.018 mol of sodium nitrite in 10 mL of water and slowly drip into the flask.After the completion of the dropwise addition, the reaction was carried out for 0.5 h to obtain a yellow diazonium salt solution.0.0 ImoL furfural dissolved in 1 mL of acetone and stirred for 30 minutes.The prepared diazonium salt solution was dropped into the flask, and the temperature of the system was maintained at 10 ° C in an ice water bath for 3 hours.After the reaction, the mixture was washed with water (2×30 mL), washed with a saturated sodium chloride solution (1×40 mL), and filtered to give a crude product.The ethanol was recrystallized to give the product 1.22 g, yield: 53.6percent, 20 mL of distilled water and 14 mL of concentrated hydrochloric acid were added to p-chloroaniline (2.55 g, 20 mmol). The mixture was heated to 70 ° C and dissolved completely. After cooling to 0 ° C, a solution of sodium nitrite Dissolved in 10mL distilled water, 20mmol), drop complete, clarify the reaction, continue the reaction 20min, adding furfural (2.88g, 30mmol)And copper chloride (0 54 g, 4 mmol), the reaction liquid was green, Stirring overnight, the precipitation of brown solids, filter solid brown-green, filter cake followed by a small amount of water, Saturated sodium carbonate solution and petroleum ether washing, Yellow solid, solid with methanol / ethanol recrystallization, activated carbon decolorization, in silver-gray solid, the yield was 25.4percentGeneral procedure: 1.00 mmol arylhalide, 1.30 mmol furfural-boronic acid and 0.05 mmolBis(triphenylphosphine)palladium(II) dichloride were treated with 0.30 mLdimethoxyethane, 0.50 mL ethanol and 0.30 mL aqueous 2M sodium carbonate solution.The reaction was heated to 65°C for 1h or until the TLC showed no remaining startingmaterial. The mixture was evaporated and extracted three times with ethyl acetate. Thecombined organic layers were washed with brine, dried over MgSO4, filtered andconcentrated. The crude product was purified by column chromatography usinghexanes/ethyl acetate (9:1).General procedure: To a solution of 1-bromo-4-chlorobenzene (478 mg, 2.50 mmol) in a mixture of DME (7.5 mL) and EtOH (5.0 mL) were added PdClA.

Molecular Weight:206.62
XLogP3:3.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:206.0134572
Monoisotopic Mass:206.0134572
Topological Polar Surface Area:30.2
Heavy Atom Count:14
Complexity:200
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes