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500536-40-3

1-Bromo-2-chloro-4,5-dimethylbenzene synthesis

3synthesis methods
-

Yield:500536-40-3 69.2%

Reaction Conditions:

with hydrogenchloride;copper(l) chloride;sodium nitrite in water at 0 - 20; for 0.333333 h;

Steps:

1-Bromo-2-chloro-4,5-dimethylbenzene (iii)

To a suspension of aniline ii (20.0 g, 100 mmol) in H2O (50 mL)was added 12 M HCl (100 mL) and the reaction mixture was cooled to 0 °C, to which was gradually added NaNO2 (8.99 g, 130 mmol) in H2O (30 mL) followed by CuCl (12.1 g, 122 mmol) dissolved in 12 M HCl (30 mL) at same temperature. After warmed up to room temperature, the reaction was stirred for further 20 min. The products were extracted with Et2O (X3), and the combined organic extracts were washed with 25% NH3 aq. and brine, dried (Na2SO4), and concentrated in vacuo. Purification of the crude products by recrystallization from MeOH gave 1-bromo-2-chloro-4,5-dimethylbenzene (iii) (15.2 g, 69.2%) as colorless prisms.

References:

Eda, Shohei;Hamura, Toshiyuki [Molecules,2015,vol. 20,# 10,p. 19449 - 19462] Location in patent:supporting information