5-Bromo-2-chlorobenzyl amine

To a solution of 5-bromo-2-chloro-benzamide (7.5 g, 32 mmol) in 200 mL of THF was added BH3 (10M, 16 mL) dropwise at 0 °C and the reaction mixture was stirred at 85 °C for 10 hours. Then the reaction was quenched with 2N HCI (30 mL) and heated to reflux for 1 hour. After adjusting to pH = 8 with NaHC03 aq., extraction with EtOAc (200 mL), drying over Na2S05-Bromo-2-chlorobenzylamine (3); [00102] To a solution of the azide 2 (2.4 g, 9.76 mmol) in THF (60 mL) at 0 °C was added triphenylphosphine (2.86 g, 10.90 mmol, 1.12 eq) slowly with stirring. After addition, the mixture was stirred at 0 °C for 10 min and at room temperature overnight. TLC analysis (EtOAc-hexanes, 1 :20) showed that the starting material disappeared. Ammonium hydroxide solution (10 mL) was added dropwise. After stirring for 30 min, IN NaOH solution (20 mL) was added, the resulting mixture was stirred at room temperature for 2 h. Ether (100 mL) and water (80 mL) were added. The mixture was made acidic (pH 2) by adding 4N HTo a stirred solution of 2-chloro-X-bromobenzylamine derivative (1 equiv.) in dioxane/water (6/1 , 5 mL/mmol) under azote atmosphere, were added sodium carbonate (2 equiv.), 2, 2-dimethylethenylboronic acid (1 .1 equiv.) and 1 , 1 '-bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (0.1 equiv.). The reaction mixture was warmed to 90C overnight. Then, the reaction mixture was partitioned between EtOAc and H20. The layers were separared and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over Na2S04 and concentrated. Purification of the crude was achieved by flash column chromatography (0-10% MeOH in DCM) to give the expected compound.The following compounds are examples illustrating this procedure:; [2-chloro-5-(2-methylprop-1 -enyl)phenyllmethanamine was prepared from (5- bromo-2-chloro-phenyl)methanamine (500 mg, 2.27 mmol). Yield: 248 mg (56%) of the title compound as a dark oil. ESI-MS: 196.2 (M+H)+.

Molecular Weight:220.49
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:218.94504
Monoisotopic Mass:218.94504
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes