Potassium Carbonate → 1,3-Dibromo-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

HRID 532148노트

반응식

HRID 532148 반응식
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([Br:8])[CH:7]=1.Br[C:13]([C:15]([F:18])([F:17])[F:16])=[CH2:14].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:13]([C:15]([F:18])([F:17])[F:16])=[CH2:14])[CH:5]=[C:6]([Br:8])[CH:7]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 27346893,5-Dibromobenzeneboronic acid

생성물 1

HCID 593789071,3-Dibromo-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene수율 76%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

A mixture of 3,5-dibromophenylboronic acid (2.58 g, 9.2 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (2.42 g, 13.8 mmol), K2CO3 (2.54 g, 18.4 mmol) and Pd(PPh3)2Cl2 (129 mg, 0.18 mmol) in THF (12 mL) and H2O (6 mL) was heated at 80° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between EA (50 mL) and H2O (50 mL). The aqueous layer was extracted with EA (50 mL) and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel to give the crude desired product (2.3 g; 76% yield) as colorless oil.

후처리

  1. temperatureThe mixture was cooled to rt
  2. custompartitioned between EA (50 mL) and H2O (50 mL)
  3. extractionThe aqueous layer was extracted with EA (50 mL)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-02eb3b8d08cf447eb0ea6cd7e8d9f385
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853186B2

반응 노트

불러오는 중…