2-Aminophenol → 5-(1,3-Benzoxazol-2-yl)-2-methylphenol

To a 100 mL round-bottom flask with 3-hydroxy-4-methylbenzoic acid (2.5 g, 16.4 mmol), was added SOCl2 (15 mL) dropwise. The reaction was refluxed for 30 min, cooled to rt and the excess of SOCl2 was removed in vacuo. The oily acid chloride was dissolved in THF (15 mL) and the solution was added dropwise to a mixture of 2-aminophenol (1.8 g, 16.4 mmol), triethylamine (1.7 g, 16.4 mmol) and THF (30 mL) at 0° C. The reaction was then warmed to rt for 1 h and the precipitate was removed by filtration. The filtrate was concentrated and dried in vacuo and the dark brown solid residue was dissolved in toluene (20 mL) and p-toluenesulfonic acid (15.6 g, 82 mmol) was added. The reaction was refluxed overnight, cooled to rt and dissolved in EtOAc (500 mL). The organic solution was washed with brine (3×50 mL), dried (MgSO4), filtered, and concentrated in vacuo. The residue was recrystallized in EtOAc to afford 5-(1,3-benzoxazol-2-yl)-2-methylphenol as a light yellow solid. MS (ESI) 226 (M+H)+.

1. temperatureThe reaction was refluxed for 30 min
2. customthe excess of SOCl2 was removed in vacuo
3. dissolutionThe oily acid chloride was dissolved in THF (15 mL)
4. temperatureThe reaction was then warmed to rt for 1 h
5. customthe precipitate was removed by filtration
6. concentrationThe filtrate was concentrated
7. customdried in vacuo
8. dissolutionthe dark brown solid residue was dissolved in toluene (20 mL)
9. temperatureThe reaction was refluxed overnight
10. temperaturecooled to rt
11. washThe organic solution was washed with brine (3×50 mL)
12. dry with materialdried (MgSO4)
13. filtrationfiltered
14. concentrationconcentrated in vacuo
15. customThe residue was recrystallized in EtOAc

ORD 기록

ord-10019520ef6f48319b08b25838da63f4

출처 데이터셋

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07087601B2