Ethanolamine → 2-[(4-Bromo-3-methylphenyl)amino]ethan-1-ol

Participants

Role	Name	HCID	Charge
Reactant	Ethanolamine	HCID 700	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	L-Proline	HCID 145742	—
Reactant	2-Bromo-5-iodotoluene	HCID 2735574	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2-[(4-Bromo-3-methylphenyl)amino]ethan-1-ol	HCID 28574942	81%

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of 2-bromo-5-iodotoluene (1.60 g, 5.40 mmol), 2-aminoethanol (0.49 mL, 8.14 mmol), CuI (53.3 mg, 0.28 mmol), L-proline (63.4 mg, 0.55 mmol) and K2CO3 (1.49 g, 10.8 mmol) in DMSO (3.24 mL) was stirred at 60° C. for 12 hours. The reaction mixture was cooled and then diluted with AcOEt, and the organic layer was sequentially washed with H2O and saturated brine. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/AcOEt=1/1) to give 2-(4-bromo-3-methyl-phenylamino)-ethanol as a brown solid (1.00 g, 81%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09169254B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-13de300069af41e199aa40862afcac30
Source note	uspto-grants-2015_10