Boron tribromide → 3-Chloro-5-(2-chloro-3-fluoro-5-hydroxyphenoxy)benzonitrile

HRID 1157420노트

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HRID 1157420 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15]([O:17]C)[CH:14]=[C:13]([F:19])[C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([F:19])[C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 445492473-Chloro-5-(2-chloro-3-fluoro-5-methoxyphenoxy)benzonitrile

생성물 1

HCID 445509693-Chloro-5-(2-chloro-3-fluoro-5-hydroxyphenoxy)benzonitrile수율 35%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Under nitrogen atmosphere, 3-chloro-5-(2-chloro-3-fluoro-5-methoxyphenoxy)-benzonitrile (50-4) (9.6 g, 30.8 mmol) was diluted in CH2Cl2 (60 mL, 0.5M) and then cooled to 0° C. To this solution BBr3 (61.5 mL, 61.5 mmol, 1M in CH2Cl2) was slowly added to the reaction. The reaction mixture was allowed to slowly warm to room temperature and stir for 12 hours. It was then cooled to 0° C. and slowly quenched with water (60 mL). The aqueous layer was then extracted with methylene chloride (3×30 mL). The organic extracts were dried over sodium sulfate and concentrated. Silica gel chromatography (1%-20% EtOAc/Hexanes) gave 3-chloro-5-(2-chloro-3-fluoro-5-hydroxyphenoxy)benzonitrile (50-5) (3.2 g, 35%). LCMS (ES) m/z 298.2 (M)+.

후처리

  1. temperatureto slowly warm to room temperature
  2. temperatureIt was then cooled to 0° C.
  3. customslowly quenched with water (60 mL)
  4. extractionThe aqueous layer was then extracted with methylene chloride (3×30 mL)
  5. dry with materialThe organic extracts were dried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-525a9a5d52b949f5bab1baf7ee3f0231
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807684B2

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