Methanol → 2-((4-Bromobenzyl)amino)ethanol

To a solution of 2-(N-methylanilino)ethanol (0.76 g, 5 mmol) in methylene chloride (5 mL) were added tetraethylammonium chloride (83.0 mg, 0.5 mmol) and 0.1 mL of methanol. While stirring, a solution of bromine (0.8 g, 5 mmol) in methylene chloride (5 mL) was added slowly in a period of 5 minutes. When the color of the bromine persisted, triethylamine (0.75 mL) was added dropwise. The reaction mixture was diluted by ethyl acetate, washed with saturated sodium bicarbonate and brine, dried, and concentrated under reduced pressure to give 1.31 g of crude product which contained some 2,6-dibromo derivative. Flash chromatography of the crude mixture (35% ethyl acetate/hexane) gave 0.87 g (75%) of the desired product.

1. washwashed with saturated sodium bicarbonate and brine
2. customdried
3. concentrationconcentrated under reduced pressure
4. customto give 1.31 g of crude product which

ORD record

ord-b331bea50b8341399b359a762691f74c

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07074819B2