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812667-45-1

4-BROMO-2-METHOXY-BENZAMIDINE HYDROCHLORIDE synthesis

4synthesis methods
-

Yield:812667-45-1 33%

Reaction Conditions:

Stage #1: with triethylaluminum;ammonium chloride in toluene at 20; for 1.5 h;
Stage #2: 4-bromo-2-methoxybenzonitrile in toluene at 80; for 24 h;

Steps:

3

To a suspension of 5.349g (lOOmmol) of ammonium chloride in 200mL of toluene was dropped lOOmL (lOOmmol) of IM-triethylaluminum/hexane, and the mixture was stirred for 1.5 hours at room temperature. Then, to this mixture was added 8.48g (40mmol) of the compound obtained in the Manufacturing Example 2, and the mixture was stirred for 24 hours at 80°. After the reaction mixture was cooled with ice water, 30g of silica gel and 300mL of chloroform were added to the mixture and the mixture was stirred for 30 minutes under the roomtemperature. The mixture was filtrated with Celite and the residue was washed with 400mL of methanol. The organic layer was concentrated and 200mL of chloroform/methanol (9/1) solution was added to the residue. The mixture was filtrated and the filtrate was concentrated and the residue was washed sequentially with ether to give 3.47g (33%) of the title compound.

References:

WO2004/111053,2004,A1 Location in patent:Page/Page column 20