Potassium Carbonate → 4'-Bromo-4-ethoxy-2,3-difluoro-1,1'-biphenyl

HRID 1511479노트

반응식

HRID 1511479 반응식
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[C:6]([F:13])[C:5]=1[F:14])[CH3:2].[Br:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>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.C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:19]2[CH:20]=[CH:21][C:16]([Br:15])=[CH:17][CH:18]=2)=[C:6]([F:13])[C:5]=1[F:14])[CH3:2]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 15135235B-(4-Ethoxy-2,3-difluorophenyl)boronic acid

생성물 1

HCID 120674514'-Bromo-4-ethoxy-2,3-difluoro-1,1'-biphenyl수율 94%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매2회HCID 1140Toluene용매2회

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온도
25 °C

실험 절차

4-Ethoxy-2,3-difluorophenylboronic acid (7) (14.4 g), 4-bromoiodobenzene (8) (20.0 g), potassium carbonate (29.3 g), Pd(Ph3P)2Cl2 (1.49 g), toluene (100 ml), Solmix A-11 (100 ml) and water (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 2 hours. The reaction mixture was cooled to 25° C., and then poured into water (500 ml) and toluene (500 ml), and mixed. The mixture was then allowed to separate into organic and aqueous phases. The extraction into an organic phase was carried out. The organic phase obtained was washed with water and dried over anhydrous magnesium sulfate. Then, the solution was concentrated under reduced pressure, and the residue obtained was purified by means of column chromatography (silica gel; toluene). The product was further purified by means of recrystallization (Solmix A-11), giving 20.8 g of 4-ethoxy-4′-bromo-2,3-difluoro-1,1′-biphenyl (9). The yield based on the compound (8) was 94.0%.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. additionmixed
  4. customto separate into organic and aqueous phases
  5. extractionThe extraction into an organic phase
  6. customThe organic phase obtained
  7. washwas washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThen, the solution was concentrated under reduced pressure
  10. customthe residue obtained
  11. customwas purified by means of column chromatography (silica gel; toluene)
  12. customThe product was further purified by means of recrystallization (Solmix A-11)

출처 및 근거

ORD 기록
ord-c1248874aae4490ea8a3e4a93107aba7
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08216489B2

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