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

HRID 71076ノート

反応式

HRID 71076 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a1a520b893e14d86aeb986db24dcaa93
出典データセット
uspto-grants-2014_09
特許番号
US08822708B2

反応ノート

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