4-(4-bromophenoxymethyl)-1,2-dichlorobenzene synthesis

Yield:889071-55-0 100%

Reaction Conditions:

with triphenylphosphine;diethylazodicarboxylate in tetrahydrofuran;toluene at 20;

Steps:

27.A (27A) 4-[(4-Bromophenoxy)methyl]-1,2-dichlorobenzene

(27A) 4-[(4-Bromophenoxy)methyl]-1,2-dichlorobenzene 4-Bromophenol (1.07 g, 6.18 mmol), 3,4-dichlorobenzyl alcohol (1.42 g, 8.02 mmol), and triphenylphosphine (2.10 g, 8.01 mmol) were dissolved in tetrahydrofuran (30 mL), and a diethyl azodicarboxylate toluene solution (2.2M, 3.65 mL, 8.03 mmol) was slowly added dropwise thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound was obtained as a white solid (2.25 g, quantitative). ¹H NMR (CDCl₃, 400 MHz): δ4.98 (2H, s), 6.83 (2H, d, J=9.0 Hz), 7.24 (1H, m), 7.39 (2H, d, J=9.0 Hz), 7.45 (1H, d, J=8.2 Hz), 7.52 (1H, d, J=2.0 Hz)

References:

US2011/53974,2011,A1 Location in patent:Page/Page column 36