4-(BROMOMETHYL)-2,6-DI-TERT-BUTYLPYRIDINE

The mixture containing 4-Hydroxymethyl-2, 6-di-t-butylpyridine (Compound B) A heterogeneous solution of 4-bromomethyl-2, 6-di-t-butylpyridine (Compound A, 1.743 g, 82% purity) in 20 ml of 12% NaOH in water and 10 ml of 1, 4-dioxane was refluxed for 12 hours. The solution spontaneously separated into two layers as it cooled to room temperature. The upper layer was separated and ethyl acetate was added. This organic layer was then washed with brine, water and dried over MgSO4. The desired product was purified by column chromatography (ethyl acetate/hexane 1/9) to give a white solid. 1 H NMR delta 7.09 (s, 2H), . 4.67 (d, J=4.4 Hz, 2H), 2.3 (b, 1H), 1.36 (s, 18H).4-Bromomethyl-2, 6-di-t-butylpyridine (Compound A3) To a mixture of 2, 6-di-t-butyl-4-methylpyridine (Aldrich, 2.0 g, 9.73 mmol) in 25 ml of dry CCl4 was added benzoyl peroxide (24 mg, 0.097 mmol) and NBS (1.9 g, 10.7 mmol). The reaction mixture was refluxed for 16 hours. After it cooled to room temperature, the solvent was removed in vacuo and the residue was purified by column chromatography (silica gel, hexane) to give an oil (1.957 g) which contained 82percent of the desired product and 18percent of the starting material. 1 H NMR delta 7.09 (s, 2H), 4.39 (s, 2H), 1.35 (s, 18H).4-Bromomethyl-2, 6-di-t-butylpyridine (Compound A) To a mixture of 2, 6-di-t-butyl-4-methylpyridine (Aldrich, 2.0 g, 9.73 mmol) in 25 ml of dry CCl4 was added benzoyl peroxide (24 mg, 0.097 mmol) and NBS (1.9 g, 10.7 mmol). The reaction mixture was refluxed for 16 hours. After it cooled to room temperature, the solvent was removed in vacuo and the residue was purified by column chromatography (silica gel, hexane) to give an oil (1.957 g) which contained 82percent of the desired product and 18percent of the starting material. 1 H NMR delta 7.09 (s, 2H), 4.39 (s, 2H), 1.35 (s, 18H).

Molecular Weight:284.23
XLogP3:4.8
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:283.09356
Monoisotopic Mass:283.09356
Topological Polar Surface Area:12.9
Heavy Atom Count:16
Complexity:202
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes