Boron tribromide → 3-(6-(Dibenzo[b,d]thiophen-4-yl)pyridin-2-yl)phenol

HRID 71076노트

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HRID 71076 반응식
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26]C)[CH:21]=3)[N:15]=2)=[CH:3][CH:2]=1.B(Br)(Br)Br>ClCCl>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4]([C:14]2[N:15]=[C:16]([C:20]3[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=3)[CH:17]=[CH:18][CH:19]=2)=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 594892612-(Dibenzo[b,d]thiophen-4-yl)-6-(3-methoxyphenyl)pyridine

생성물 1

HCID 594892693-(6-(Dibenzo[b,d]thiophen-4-yl)pyridin-2-yl)phenol수율 109.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

2-(dibenzo[b,d]thiophen-4-yl)-6-(3-methoxyphenyl)pyridine (3.8 g, 10.3 mmol) was dissolved in 120 mL dichloromethane. The solution was cooled to 0° C. under nitrogen. BBr3 (22.8 mL, 1M in hexane) was slowly added in at 0° C. and then was slowly brought up to room temperature. The mixture was stirred at room temperature overnight. A brown solid was observed to form. The reaction was quenched by adding 100 mL water slowly. The dichloromethane was removed by rotovap. Then the mixture was refluxed for three hours. Saturated sodium bicarbonate solution was added to neutralize the mixture, which was extracted by dichloromethane and ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain 4 gram glassy dark brown solid. The product was used for next step without further purification.

후처리

  1. customwas slowly brought up to room temperature
  2. customto form
  3. customThe reaction was quenched
  4. additionby adding 100 mL water slowly
  5. customThe dichloromethane was removed by rotovap
  6. temperatureThen the mixture was refluxed for three hours
  7. additionSaturated sodium bicarbonate solution was added
  8. extractionwas extracted by dichloromethane and ethyl acetate
  9. dry with materialThe combined organic layers were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a1a520b893e14d86aeb986db24dcaa93
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822708B2

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