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ChemicalBook CAS DataBase List 3-Bromo-2-methylfuran
83457-06-1

3-Bromo-2-methylfuran synthesis

3synthesis methods
-

Yield:-

Reaction Conditions:

bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran at 20;

Steps:

222.A

Example 222.; Preparation of 8-(1-ethyl-propyl)-2,6-dimethyl-3-(2-methyl-furan-3-yl)-imidazo[1,2- b]pyridazine.; A. 3-Bromo-2-methyl furan.; A THF solution (10 mL) of 2,3-dibromofuran (Lancaster, 5.54 gm, 24.5 mmol) under N2 is treated with PdCl2(PPh3)2 (860 mg, 1.2 mmol) and stirred for 10 minutes at EPO room temperature. The solution is then treated with CH3ZnCl (Aldrich, 2.0 M in THF, 15 mL, 30 mmol). The resulting mixture is stirred at room temperature overnight then poured into 1 N HCl and extracted into diethyl ether. The organic extract is washed with sat. NaCl, dried over Na2SO4, and filtered. The filtrate is then distilled and the product is collected at 120-125 °C to give the title compound as a colorless oil (1.71 gm, 43% yield). 1H NMR (400 mHz, CDCl3): δ 7.25 (d, J = 1.8 Hz, 1H), 6.34 (d, J = 1.8 Hz, 1H), 2.28 (s, 3H).

References:

WO2006/102194,2006,A1 Location in patent:Page/Page column 161-162

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