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ChemicalBook CAS DataBase List 4-FLUORO-2-METHYLPHENYLMAGNESIUM BROMIDE
30897-90-6

4-FLUORO-2-METHYLPHENYLMAGNESIUM BROMIDE synthesis

1synthesis methods
-

Yield:-

Reaction Conditions:

with iodine;magnesium;magnesium bromide in tetrahydrofuran; for 1 h;Reflux;Inert atmosphere;Grignard Reaction;

Steps:

19.1 1-Benzyl-4-(4-fluoro-2-methylphenyl)-1,2,3,6-tetrahydropyridine (10)

A mixture of Mg (turnings, 48.6 mg, 2.00 mmol), 1-bromo-4-fluoro-2-methylbenzene (Tokyo Chemical Industry, 253 μL, 2.00 mmol), iodine (25.4 mg, 0.100 mmol), and MgBr2 (7.0 μL, 0.10 mmol) in anhydrous THF (5.0 mL) was stirred under reflux conditions under N2 for 1 h, and cooled to room temperature.
To the resulting solution of Grignard reagent (4-fluoro-2-methylphenylmagnesium bromide) was added a solution of 1-benzyl-4-piperidone (Tokyo Chemical Industry, 371 μL, 2.00 mmol) in anhydrous THF (7.0 mL) at room temperature under N2 within 5 min.
The mixture was stirred at room temperature under N2 for 10 min, then stirred under reflux conditions for 6 h.
The reaction solution was cooled to 0 °C then poured into ice-cooled aqueous NH4Cl (40 mL).
The mixture was extracted with CH2Cl2 (40 * 4), then the combined extracts were dried over anhydrous MgSO4 and concentrated in vacuo to afford 658.5 mg of 1-benzyl-4-(4-fluoro-2-methylphenyl)piperidin-4-ol 9 (crude). TLC: Rf = 0.4, AcOEt/hexane = 1:8.
To a stirred solution of 1-benzyl-4-(4-fluoro-2-methylphenyl)piperidin-4-ol 9 (658.5 mg, crude) in toluene (50.0 mL) was added p-toluenesulfonic acid monohydrate (760.1 mg, 4.00 mmol) under N2 at room temperature.
The resulting solution was heated to reflux and stirred under N2 for 10 h.
The solution was cooled to 0 °C, basified by adding 2 N NaOH (30 mL), then the mixture was extracted with chloroform (50 mL * 2).
The combined extracts was dried over anhydrous MgSO4, and concentrated in vacuo.
The residue was purified by flash column chromatography (silica gel, CH2Cl2/MeOH = 36:1) to afford 343.3 mg of the title product 10 in 61% yield (2 steps) as a yellow oil. 1H NMR (270 MHz, CDCl3) δ 7.40-7.24 (5H, m, Ar H), 7.05 (1H, dd, J = 8.24 Hz, J = 6.10 Hz, Ar H), 6.88-6.77 (2H, m, Ar H) 5.53-5.49 (1H, m, CH), 3.65 (2H, s, Ph-CH2-N), 3.13 (2H, dd, 5.91 Hz, 2.81 Hz, N-CH2), 2.68 (2H, t, 5.62 Hz, N-CH2), 2.36-2.29 (2H, m, CH2), 2.28 (3H, s, Ar-CH3).

References:

Hayashi, Shigeo;Ohashi, Katsuyo;Nakata, Eriko;Emoto, Chie [European Journal of Medicinal Chemistry,2012,vol. 55,p. 228 - 242]

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