4-Fluoroaniline → 2-(4-Fluoroanilino)ethan-1-ol

Temperature

80 °C

A mixture of 4-fluoroaniline (1.0 g, 8.99 mmol), 2-bromoethanol (2.25 g, 17.99 mmol), potassium carbonate (2.49 g, 17.99 mmol), and anhydrous N,N-dimethylformamide (4 mL) was added to a 50 mL RBF with a magnetic stirring bar. The mixture was allowed to stir at 80° C. for 18 hours. Progress of the reaction was monitored by TLC using ethyl acetate:hexanes (1:1) (Rf product=0.4). The reaction was partitioned using ethyl acetate (80 mL) and water (30 mL). The organic layer was washed with saturated aqueous NaCl (3×30 mL), dried (Na2SO4), filtered, and concentrated. The crude material was purified by silica gel column chromatography using a gradient elution of 30-100% ethyl acetate in hexanes to afford the title compound as an oil (0.75 g, 54% yield).

1. additionwas added to a 50 mL RBF with a magnetic stirring bar
2. customThe reaction was partitioned
3. washThe organic layer was washed with saturated aqueous NaCl (3×30 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude material was purified by silica gel column chromatography
8. washa gradient elution of 30-100% ethyl acetate in hexanes

ORD record

ord-771338b15cc345f9a4d37e23acfafa50

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09163027B2