Isopropanol → 2,3',5'-Trifluoro[1,1'-biphenyl]-4-ol

HRID 444654노트

반응식

HRID 444654 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[F:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[C:15]([F:17])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CC(O)C>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>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]2[CH:12]=[C:11]([F:10])[CH:16]=[C:15]([F:17])[CH:14]=2)=[C:3]([F:9])[CH:4]=1

참가 물질

8

반응물 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 27791534-Bromo-3-fluorophenol

생성물 1

HCID 532193752,3',5'-Trifluoro[1,1'-biphenyl]-4-ol수율 74%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
25 °C

실험 절차

4-Bromo-3-fluorophenol (T-1) (50.0 g), 3,5-difluorophenylboronic acid (45.5 g), potassium carbonate (72.4 g), Pd(Ph3P)2Cl2 (5.52 g) and 2-propanol (500 ml) were put in a reaction vessel and heated to reflux for 5 hours under an atmosphere of nitrogen. After the reaction solution had been cooled to 25° C., it was poured into water (500 ml) and mixed with it. Toluene (500 ml) was added to the solution to separate organic and aqueous phases, and extraction was carried out. The combined organic phase was washed with water and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure and the residue was purified with a fractional operation by means of column chromatography (silica gel; toluene). The product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11 and dried, giving 4-hydroxy-2,3′,5′-trifluoro-1,1′-biphenyl (T-2) (43.4 g). The yield based on the compound (T-1) was 74%.

후처리

  1. temperatureheated
  2. temperatureto reflux for 5 hours under an atmosphere of nitrogen
  3. additionmixed with it
  4. customto separate organic
  5. extractionaqueous phases, and extraction
  6. washThe combined organic phase was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe resulting solution was concentrated under reduced pressure
  9. customthe residue was purified with a fractional operation by means of column chromatography (silica gel; toluene)
  10. customThe product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11
  11. customdried

출처 및 근거

ORD 기록
ord-f6431f45bf2b4cfe8d41b1b94bcf3602
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08475888B2

반응 노트

불러오는 중…