Benzene → 1-Bromo-4-ethylbenzene

Employing the same general procedure as for the preparation of 5-bromo-2-tert-butyl-1-[(2′-amino-4′-methyl)phenoxy]benzene (Compound I), 781 mg (3.4 mmol) of 5-bromo-2-tert-butylphenol (Compound H) was converted into crude 5-bromo-2-tert-butyl-1-[4′-ethyl-2′-nitro)phenoxy]benzene using 611 mg (5.0 mmol) of potassium t-butoxide, 1.0 g (5.25 mmol) of cuprous iodide, 770 mg (˜2.78 mmol) of 1-bromo-4ethyl-2-nitrobenzene (˜80% purity, obtained from the nitration of 1-bromo-4-ethylbenzene) and 10 mL of pyridine. Purification by flash chromatography (silica, 5% ethyl acetate in hexane) gave crude 5-bromo-2-tert-butyl-1-[(4′-methyl-2′-nitro)phenoxy]benzene as a yellow oil. 290 mg of this crude sample was converted into the title compound using a balloon filled with hydrogen, 31 mg of 10% Pd/C, 4 mL of acetonitrile and 1 mL of methanol. Purification by flash chromatography (silica, 2% ethyl acetate in hexane) gave the title compound as a yellow oil. PMR (CDCl3): δ 1.24 (3 H, t, J=7.5 Hz), 1.44 (9 H, s), 2.58 (2 H, q, J=7.5 Hz), 3.72 (2 H, br s), 6.57 (1 H, dd, J=2.1, 8.2 Hz), 6.68-6.74 (2 H, m), 6.81 (1 H, d, J=2.1 Hz), 7.09 (1 H, dd, J=2.1, 8.4 Hz), 7.22 (1 H, d, J=8.4 Hz).

ORD record

ord-55a48516f9c84df38df31cd176e803eb

Source dataset

uspto-grants-2001_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06187950B1