Toluene → Methyl 5-(4-phenylphenyl)thiophene-2-carboxylate

HRID 1892084노트

반응식

HRID 1892084 반응식
Br[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.[C:11]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[C:11]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:16]=[CH:15][C:14]([C:2]2[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 605713Methyl 5-bromothiophene-2-carboxylate

생성물 1

HCID 12317965Methyl 5-(4-phenylphenyl)thiophene-2-carboxylate수율 75.2%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

A mixture of compound 1021 (5.0 g, 22.6 mmol), biphenyl-4-ylboronic acid (5.4 g, 27.1 mmol), sodium carbonate (5.9 g, 56.5 mmol), tetrakis(triphenylphosphine)palladium(0) (2.65 g, 2.3 mmol), toluene (200 mL), ethanol (100 mL) and water (50 mL) was heated to reflux for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, and extracted with dichloromethane (2×250 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography with silica gel (5% EtOAc in hexane) to give compound 1022 (5.0 g). 1H NMR (CDCl3, 300 MHz) δ 3.92 (s, 3H), 7.32-7.49 (m, 4H), 7.62-7.80 (m, 7H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours under nitrogen atmosphere
  3. extractionextracted with dichloromethane (2×250 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash chromatography with silica gel (5% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-82caae39f2b942b092f05e988f10f05f
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507647B2

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