Water → 7-Amino-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one

HRID 14469노트

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HRID 14469 반응식
[NH2:1][C:2]1[C:11]([O:12]C)=[C:10]2[C:5]([C:6](=[O:24])[C:7]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[C:8]([CH:14]([CH3:16])[CH3:15])[O:9]2)=[CH:4][CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[NH2:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([C:6](=[O:24])[C:7]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)=[C:8]([CH:14]([CH3:15])[CH3:16])[O:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 597242827-Amino-3-(4-chlorophenyl)-2-isopropyl-8-methoxy-chromen-4-one

생성물 1

HCID 687013867-Amino-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

A stirred solution of 7-amino-3-(4-chlorophenyl)-2-isopropyl-8-methoxy-chromen-4-one (0.178 g, 0.52 mmol) in methylene chloride (5 ml) under an argon atmosphere is cooled to −78° C. and treated with boron tribromide (1M solution in methylene chloride, 3.2 ml, 3.2 mmol, 6.2 eq.). The reaction mixture is stirred at −78° C. for 1 h and at room temperature for 45 min, whereupon HPLC analysis indicates that the reaction is complete. The reaction mixture is treated with water (32 ml) and stirred at ambient temperature overnight. The mixture is washed with methylene chloride, and the organic layer is washed with 5% sodium thiosulfate solution, followed by brine. The organic phase is dried over anhydrous magnesium sulfate and filtered, and the solvent is removed by evaporation in vacuo to afford a brown oil. The oil is purified by flash chromatography (hexane/ethyl acetate=9:1 through 1% methanol in ethyl acetate to methylene chloride/methanol=9:1) to afford the title compound.

후처리

  1. stirringstirred at ambient temperature overnight
  2. washThe mixture is washed with methylene chloride
  3. washthe organic layer is washed with 5% sodium thiosulfate solution
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed by evaporation in vacuo
  7. customto afford a brown oil
  8. customThe oil is purified by flash chromatography (hexane/ethyl acetate=9:1 through 1% methanol in ethyl acetate to methylene chloride/methanol=9:1)

출처 및 근거

ORD 기록
ord-c4b4b48c40bd4418a391d32bbacdd752
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732435B2

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