Ethyl Acetate → HCID 67083826, compound

Temperature

70 °C

To a solution of 2-bromo-5-nitrophenol (7.24 g, 33.2 mmol) (Method 9) in anhydrous DMF was added 2-methoxy-1-bromoethane (6.92 g, 49.8 mmol) and a catalytic amount of potassium iodide (˜100 mg). The reaction was heated at 70° C. for 4 h before being allowed to cool to rt. The reaction was then poured into a separatory funnel and partitioned between EtOAc (˜250 mL) and water (˜250 mL). The organic phase was dried over Na2SO4 and conc in vacuo giving the crude title compound which was taken up in a minimum volume of warm EtOAc. The resulting solution was cooled in an ice bath and hexanes were slowly added to induce crystallization. The resulting precipitate was isolated via vacuum filtration through a fritted funnel and air dried to give pure title compound (8.3 g, 91%). 1H NMR: (300 MHz) 7.87-7.92 (m, 2H), 7.76 (dd, 1H), 4.35 (t, 2H), 3.73 (t, 2H), 3.35 (s, 3H).

1. temperatureto cool to rt
2. additionThe reaction was then poured into a separatory funnel
3. custompartitioned between EtOAc (˜250 mL) and water (˜250 mL)
4. dry with materialThe organic phase was dried over Na2SO4 and conc in vacuo
5. customgiving the crude title compound which
6. temperatureThe resulting solution was cooled in an ice bath
7. customcrystallization
8. customThe resulting precipitate was isolated via vacuum filtration through a fritted funnel
9. customair dried

ORD record

ord-4d1dc60eb9c24351aae4a4652e41adcc

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723337B2