Boron tribromide → 4-(4'-Hydroxyphenoxy)biphenyl

HRID 749936노트

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HRID 749936 반응식
C[O:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O.ClCCl>ClCCl>[C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:20]=[CH:21][C:3]([OH:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 2668644-(4-Methoxyphenoxy)biphenylHCID 21908982Water methylene chloride

생성물 1

HCID 105634264-(4'-Hydroxyphenoxy)biphenyl수율 50.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

To a solution of the product from step 1 (0.5 g, 1.81 mmol) in dichloromethane (10 mL) at −78° C. was added boron tribromide (1.0 M solution in dichloromethane, 5.43 mL, 5.43 mmol) dropwise over 5-10 min. The subsequent mixture was stirred at −78° C. for an hour followed by ambient temperature for 1 h. After cooling the reaction mixture to 0° C., it was slowly added to cold water/dichloromethane (50 mL/50 mL). The organic portion was washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.24 g, 47%) as an off-white solid.

후처리

  1. temperatureAfter cooling the reaction mixture to 0° C.
  2. washThe organic portion was washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-217571d23617411da9d8bb5774b30b90
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402684B2

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