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Boron tribromide → 6-Ethyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indol-4-ol

HRID 2421255
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HRID 2421255 반응식
[CH2:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([F:20])[CH:13]=2)=[C:5]([O:21]C)[CH:4]=1)[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([C:3]1[CH:4]=[C:5]([OH:21])[C:6]2[CH:7]=[CH:8][N:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:20])[CH:13]=3)[C:10]=2[CH:11]=1)[CH3:2]
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참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 596279376-Ethyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole

생성물 1

HCID 441931886-Ethyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indol-4-ol수율 4.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 6-ethyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole (D10) (180 mg, 0.60 mmol) in dichloromethane (6 mL) at −78° C. was added boron tribromide (1 M solution in dichloromethane, 2.5 mL, 2.5 mmol). The reaction mixture was allowed to warm to 0° C. and then quenched by the addition of water and dichloromethane. The solution was neutralised by the addition of dilute sodium hydrogen carbonate solution. The organic phase was separated and then the aqueous phase re-extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated at reduced pressure. The product was purified by MDAP to yield the title compound (E6), (8 mg).

후처리

  1. customquenched by the addition of water and dichloromethane
  2. additionThe solution was neutralised by the addition of dilute sodium hydrogen carbonate solution
  3. customThe organic phase was separated
  4. extractionthe aqueous phase re-extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customThe product was purified by MDAP

출처 및 근거

ORD 기록
ord-b2256c0ba64f4d41bbed2ab04154f8ef
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07956083B2

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