5-BROMO-2,4-DIMETHYLPYRIDINE
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5-BROMO-2,4-DIMETHYLPYRIDINE
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CAS No:
27063-92-9
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Formula:
C7H8BrN
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Chemical Name:
5-BROMO-2,4-DIMETHYLPYRIDINE
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Synonyms:
5-BROMO-2,4-DIMETHYLPYRIDINE;PYRIDINE, 5-BROMO-2,4-DIMETHYL-
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CAS No:
5-BROMO-2,4-DIMETHYLPYRIDINE Use and Manufacturing
To a three-neck flask, was placed B12.1 (2.51 g, 10.0 mmol) in dry THF (50 mL), Pd(PPhBromination of 2, 4-lutidineTo 2, 4-lutidine (5.39 mL, 46.7 mmol, 1 eq.) was added oleum (50 mL, containing 20percent free SO[0668] To a mixture of Example 165a (186 mg, 1.00 mmol) in dioxane (3 mL) were added (BPin)2 (305 mg, 1.29 mmol), Pd(dppf)Cl2 (73 mg, 0.10 mmol) and KOAc (294 mg, 3.00 mmol). The mixture was stirred at 100C for 45 min under N2 by microwave. The crude mixture Example 165b was used in the next step directly.To a three-neck flask, was placed B12.1 (2.51 g, 10.0 mmol) in dry THF (50 mL), Pd(PPh3)4 (1.15 g, 1.0 mmol). The mixture was protected under N2 and stirred at 0 oC. MeMgBr/THF (15 mL, 15.0 mmol, 1 mol/L) was added slowly. After addition, the mixture was refluxed for 3 h, cooled to rt, quenched the reaction mixture with 1N HCl and extracted with EtOAc (100 mL × 3). The organic layer was washed with H2O (50 mL × 2) and brine (50 mL), then dried over anhydrous Na2SO4 and concentrated under vacuum and the crude product was purified by Biotage flash chromatography (PE/EtOAc = 5%-10%) to afford the title compound (301 mg, 16.2%) as a colorless oil.1H NMR (400 MHz, CDCl3) delta ppm 2.35 (d, 3H), 2.47 (s, 3H), 7.04 (s, 1H), 8.50 (s, 1H).
Computed Properties
Molecular Weight:186.05
XLogP3:2.3
Hydrogen Bond Acceptor Count:1
Exact Mass:184.98401
Monoisotopic Mass:184.98401
Topological Polar Surface Area:12.9
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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