Phosphorus oxybromide → 2-(3-(Bromomethyl)phenyl)-5-methyloxazole

HRID 41603

反応式

HRID 41603 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH2:13]O)[CH:10]=[CH:11][CH:12]=2)=[N:4][CH:3]=1.P(Br)(Br)([Br:17])=O.C([O-])(O)=O.[Na+]>C1COCC1>[Br:17][CH2:13][C:9]1[CH:8]=[C:7]([C:5]2[O:6][C:2]([CH3:1])=[CH:3][N:4]=2)[CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 67252704(3-(5-Methyloxazol-2-yl)phenyl)methanol

生成物 1

HCID 672511652-(3-(Bromomethyl)phenyl)-5-methyloxazole収率 84.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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].

後処理

  1. temperatureheated at 60° C. for 4 h
  2. temperatureThe mixture was cooled to rt
  3. extractionextracted with TBME (2×)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash-column chromatography over silicagel (eluent: gradient 5%-40% ethyl acetate/heptane)

出典と根拠

ORDレコード
ord-cf9487623ced493abc93547ac99c8ce5
出典データセット
uspto-grants-2013_09
特許番号
US08530648B2

関連ノート

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