Hydroquinone → N-(4-bromophenyl)-2-(4-hydroxyphenoxy)acetamide

Temperature

80 °C

A mixture of compound 7a (496 mg, 2 mmol), K2CO3 (553 mg, 4 mmol), and KI (66 mg, 0.4 mmol) in DMF (50 mL) was bubbled with argon for 10 min Hydroquinone (440 mg, 4 mmol) was added to the mixture under argon. The reaction mixture was heated and stirred at 80° C. for 6 hr. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 100 mL water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with EtOAc and the combined organic layer was washed with water, then brine, and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/EtOAc (3:1) to provide the intermediate 7b (100 mg, 0.3 mmol, 16% yield). 1H NMR (400 MHz, Chloroform-d) δ 8.30 (broad s, 1H), 7.56-7.46 (m, 4H), 6.94-6.87 (m, 2H), 6.87-6.80 (m, 2H), 4.57 (s, 2H).

1. additionwas added to the mixture under argon
2. temperatureThe reaction mixture was heated
3. temperatureAfter cooling to room temperature
4. customthe solvent was evaporated
5. customthe residue was quenched with 100 mL water
6. extractionThe mixture was then extracted with EtOAc
7. washthe combined organic layer was washed with water
8. dry with materialbrine, and dried over Na2SO4
9. customThe solvent was evaporated
10. customthe residue was purified by silica gel column chromatography with hexane/EtOAc (3:1)

ORD record

ord-fdcc8f689a094b5fb261a2812c4f25dd

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394233B2