2-chloro-5-nitropyrimidine

Step 1: General procedure: Compound 1a, 1b, 3a, 3b, 7a, or 7b, 0.57 mmol, was added with vigorous stirring at 20°C to a solution of 0.2 mL (2.6 mmol) of trifluoroacetic acid in 3 mL of methylene chloride, 136 mg (0.57 mmol) of lead(IV) oxide was then added, and the mixture was stirred for 2–70 h. When the reaction was complete, the mixture was treated with water (50 mL) and extracted with chloroform (3 ×50 mL). The combined extracts were washed with water, a saturated aqueous solution of NaHCO3, and water again and dried over Na2SO4, and the solvent was distilled off. The residue was subjected to silica gel column chromatography using petroleum ether–ethyl acetate as eluent. Given below are the yields of the isolated compounds.Step 1: A solution of 2, 5-dibromoxylene (2.0 g, 7.6 mmol) in DCM (20 ml) was treated with n-BuLi (2.5 M solution in hexane, 3 ml, 1.0 equiv.) at -78C. After stirring for 1h, DMF (1.8 ml, 23 mmol, 3 eq.) was added and the solution was allowed to warm to room temperature. It was acidified to pH 2 with 5% hydrochloric acid and extracted with diethyl ether (3x50 ml). The combined organic phase was dried and evaporated and the residue was purified by column chromatography using PE:EA = 10:1 as eluent to give A solution of 2, 5-dibromoxylene (8.0 g, 30.3 mmol) in diethyl ether (120 mL) is cooled to -78 C. and then treated with n-buthyllithium (20 mL, 1.6 M in hexane). After stirring for 40 min, DMF (6 mL) is slowly added. The mixture is warmed to rt and stirred for 1 h. The mixture is cooled again to -78 C. before another portion of n-butyllithium (5 mL) is added. The reaction mixture is allowed to warm to rt and stirred for another hour. The reaction is quenched by adding 5% aq. HCl. The mixture is extracted with EA, and the extract is concentrated in vacuo. The crude product is purified by CC on silica gel eluting with heptane:EA 5:1 to give A solution of 2, 5-dibromoxylene (8.0 g, 30.3 mmol) in diethyl ether (120 ml_) is cooled to -78C and then treated with n-buthyllithium (20 ml_, 1.6 M in hexane). After stirring for 40 min, DMF (6 ml_) is slowly added. The mixture is warmed to rt and stirred for 1 h. The mixture is cooled again to -78C before another portion of n- butyllithium (5 ml_) is added. The reaction mixture is allowed to warm to rt and stirred for another hour. The reaction is quenched by adding 5% aq. HCI. The mixture is extracted with EA, and the extract is concentrated in vacuo. The crude product is purified by CC on silica gel eluting with heptane:EA 5:1 to give 4-bromo- 3, 5-dimethyl-benzaldehyde (8.2 g) as a white soft solid.Into a 100-mL round- bottom flask were placed

Molecular Weight:213.07
XLogP3:2.8
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:211.98368
Monoisotopic Mass:211.98368
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:135
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes