4-Fluoro-2-nitrobenzaldehyde

To a stirred solution containing 4-fluro-2-nitrotoluene (1a) (1.0g, 6.45mmol) in 15ml of anhydrous 62 N, N-dimethylformamide, was added 63 pyrrolidine (0.69g, 9.70mmol) and N, N-dimethylformamide 64 dimethyl acetal (1.54g, 12.92mmol). The resulting reaction mixture was allowed to stir at 125°C for 6h and then poured into 20ml of 65 water. The product was extracted with ethyl acetate three times (20ml×3). The combined organic layers were washed successively with 30ml of water and 30ml of brine, then dried by anhydrous sodium sulfate and concentrated under reduced pressure to provide dark red oil. The oil was dissolved in 20ml of 66 THF/water (1:1, v/v) and the resultant solution was treated with 67 sodium periodate (4.13g, 19.3mmol) at 0°C. The resulting reaction mixture was allowed to stir at room temperature overnight and was filtered through Celite. The filtrate was diluted with 10ml of water and extracted by ethyl acetate three times (15ml×3). The combined organic layers were washed successively with 25ml of water and 25ml of brine, then dried by anhydrous sodium sulfate and concentrated under reduced pressure to provide dark oil that was further purified by column chromatography on silica gel (6:1 petroleum ether/ethyl acetate) to yield 68 4-fluoro-2-nitrobenzaldehyde (2a) (0.69g, 4.08mmol, 63percent) as a yellow solid [23].10864] To a stirred solution of 4-fluoro-2-nitrobenzalde- hyde (2 g, 11.83 mmol) in CH2C12 (100 mE) were added carbon tetrabromide (5.8 g, 17.75 mmol) and triphenylphosphine (9.3 g, 35.50 mmol) at 00 C. under inert atmosphere. The reaction mixture was stirred at 5 C. for 2 h. The progress of the reaction was monitored by TEC; the reaction mixture was filtered, the filtrate was concentrated under reduced pressure to obtain 1 -(2, 2-dibromovinyl)-4-fluoro-2- nitrobenzene (3.2 g, crude) as brown solid which was used in the next step without further purification.

Molecular Weight:169.11
XLogP3:1.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:169.01752115
Monoisotopic Mass:169.01752115
Topological Polar Surface Area:62.9
Heavy Atom Count:12
Complexity:192
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes