Hydroquinone → 4-(2-Bromoethoxy)phenol

To a solution of hydroquinone (1.0 g, 9 mmol) in MeOH (15 mL), KOH (1.02 g, 9 mmol) was added and stirred at room temperature for 30 minutes under argon. 1,2-dibromoethane (0.98 mL, 11.3 mmol) was added dropwise over 10 min After the addition was complete, the mixture was refluxed for 12 hours. The reaction mixture was concentrated and was then quenched with water (50 mL) and the aqueous layer was extracted with EtOAc (2×25 mL). The combined organic layer was washed with water, then brine, and dried over Na2SO4. The solvent was evaporated to give a colorless oil, which was purified by column chromatography to isolate the intermediate 8a as a white solid (0.39 g, 1.79 mmol, 20% yield). 1H NMR (CDCl3, 400 MHz) δ 6.78-6.85 (m, 4H), 4.53 (s, 1H), 4.26 (t, J=6.4 Hz, 2H), 3.63 (t, J=6.4 Hz, 2H).

1. additionAfter the addition
2. temperaturethe mixture was refluxed for 12 hours
3. concentrationThe reaction mixture was concentrated
4. customwas then quenched with water (50 mL)
5. extractionthe aqueous layer was extracted with EtOAc (2×25 mL)
6. washThe combined organic layer was washed with water
7. dry with materialbrine, and dried over Na2SO4
8. customThe solvent was evaporated
9. customto give a colorless oil, which
10. customwas purified by column chromatography

ORD record

ord-0b4b218a430e4ed687050e2d62f6637a

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394233B2