반응 #69881

반응 방정식

NaHCO3

(3-(5-methyloxazol-2-yl)phenyl)methanol

POBr3

→

title compound

수율 84.5%

2-(3-(bromomethyl)phenyl)-5-methyloxazole

수율 84.5%

용매

THF

반응 조건

후처리

1. 1
   온도heated at 60° C. for 4 h
2. 2
   온도The mixture was cooled to rt
3. 3
   추출extracted with TBME (2×)
4. 4
   건조The combined organic layers were dried over anhydrous Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified by flash-column chromatography over silicagel (eluent: gradient 5%-40% ethyl acetate/heptane)

실험 절차

To a stirred solution of (3-(5-methyloxazol-2-yl)phenyl)methanol (0.79 g, 4.13 mmol) in THF (15 mL), POBr3 (1.93 g, 6.61 mmol) was added in portions at 5° C. The reaction mixture was allowed to warm to rt and then heated at 60° C. for 4 h. The mixture was cooled to rt, poured into saturated aqueous NaHCO3 solution and extracted with TBME (2×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash-column chromatography over silicagel (eluent: gradient 5%-40% ethyl acetate/heptane) to yield the title compound (0.88 g, 84%). [1H NMR (400 MHz, CHLOROFORM-d) ♀ ppm 8.01-8.07 (m, 1H), 7.93 (ddd, J=6.7, 2.1, 1.9 Hz, 1H), 7.39-7.47 (m, 2H), 6.85 (d, J=1.3 Hz, 1H), 4.53 (s, 2H), 2.41 (d, J=1.3 Hz, 3H); LCMS RtA=1.10, [M+H]+=252.1/254.1].

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