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ChemicalBook CAS DataBase List 3,5-Dicyanofluorobenzene

3,5-Dicyanofluorobenzene synthesis

3synthesis methods
-

Yield: 52%

Reaction Conditions:

in N,N-dimethyl-formamide for 16 h;Heating / reflux;

Steps:

38
A mixture of 3,5-dibromofluorobenzene (3Og, 120mmol) and copper (I) cyanide (42.1 g, 470mmol) in DMF (20OmL) was heated under reflux for 16h. The reaction mixture was then concentrated In vacuo and the residue was suspended in DCM (35OmL). The resulting brown precipitate was filtered through Arbocel and the filtrate was evaporated under reduced pressure. The residue was partitioned between water (5OmL) and DCM (15OmL), and the organic layer was separated, dried over sodium sulfate and concentrated in vacuo to give a yellow solid. The solid was then dissolved in diethyl ether (40OmL), washed with water (2 x 5OmL), brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound in 52% yield, 9.2g. m.p. = 98-100 0C. 1H NMR (400MHz, CD3OD) δ: 8.29 (m, 2H), 8.36 (m, 1 H).

References:

PFIZER LIMITED WO2006/67587, 2006, A2 Location in patent:Page/Page column 33

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