5-BROMO-2-METHOXYBENZYLAMINE

A solution of 5-bromo-2-methoxybenzaldehyde 11 (1 g, 4.65 mmol) and hydroxylaminehydrochloride (388 mg, 5.58 mmol) in ethanol (2.8 mL) was stirred for 1 h at room temperature.Subsequently, hydrochloric acid (12 M, 1.6 mL, 18.6 mmol) and zinc dust (760 mg, 11.62 mmol)slowly were added to the solution and the mixture was stirred at room temperature for 15 min. Asolution of ammonia (30%, 2.8 mL) and sodium hydroxide (6 M, 2.8 mL) was added dropwise tothe resulting slurry, and the mixture was stirred at room temperature for 15 min. Then, theresultant solution was extracted with CH2Cl2, dried over anhydrous sodium sulfate, and filtered.The solvent was removed under vacuum to afford the crude benzyl amine. The residue wasdissolved in CH2Cl2 (20 mL) which was then followed by the addition of Boc2O (1.52 g, 7.0mmol) and Et3N (710 mg, 7.0 mmol) at rt, the mixture was stirred for 2 h. After completion ofthe reaction, water was added into it, organic phase was separated and aqueous layer wasextracted with CH2Cl2 (3 × 20 mL). Organic phases were combined, washed with brine, driedover anhyd.Na2SO4 and concentrated to get crude boc-amine, which was then purified by columnchromatography (100-200 mesh size) using ethyl acetate:pet ether (1:9) as an eluent to affordpure boc-protected benzyl amine 12 (1.47 g).A solution of 5-bromo-2-methoxybenzaldehyde 11 (1 g, 4.65 mmol) and hydroxylaminehydrochloride (388 mg, 5.58 mmol) in ethanol (2.8 mL) was stirred for 1 h at room temperature.Subsequently, hydrochloric acid (12 M, 1.6 mL, 18.6 mmol) and zinc dust (760 mg, 11.62 mmol)slowly were added to the solution and the mixture was stirred at room temperature for 15 min. Asolution of ammonia (30%, 2.8 mL) and sodium hydroxide (6 M, 2.8 mL) was added dropwise tothe resulting slurry, and the mixture was stirred at room temperature for 15 min. Then, theresultant solution was extracted with CH2Cl2, dried over anhydrous sodium sulfate, and filtered.The solvent was removed under vacuum to afford the crude benzyl amine. The residue wasdissolved in CH2Cl2 (20 mL) which was then followed by the addition of Boc2O (1.52 g, 7.0mmol) and Et3N (710 mg, 7.0 mmol) at rt, the mixture was stirred for 2 h. After completion ofthe reaction, water was added into it, organic phase was separated and aqueous layer wasextracted with CH2Cl2 (3 × 20 mL). Organic phases were combined, washed with brine, driedover anhyd.Na2SO4 and concentrated to get crude boc-amine, which was then purified by columnchromatography (100-200 mesh size) using ethyl acetate:pet ether (1:9) as an eluent to affordpure boc-protected benzyl amine 12 (1.47 g).

Molecular Weight:216.07
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:214.99458
Monoisotopic Mass:214.99458
Topological Polar Surface Area:35.2
Heavy Atom Count:11
Complexity:121
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes