1-Iodo-4-nitrobenzene → 2-(4-Nitrophenyl)-4-methoxybenzothiophene

HRID 454801노트

반응식

HRID 454801 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[C:18]2[CH:19]=[C:20](B(O)O)[S:21][C:17]=2[CH:16]=[CH:15][CH:14]=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.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:20]2[S:21][C:17]3[CH:16]=[CH:15][CH:14]=[C:13]([O:12][CH3:11])[C:18]=3[CH:19]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

참가 물질

6

반응물 2

HCID 124951-Iodo-4-nitrobenzeneHCID 21182781(4-Methoxybenzo[b]thiophen-2-yl)boronic acid

생성물 1

HCID 469469612-(4-Nitrophenyl)-4-methoxybenzothiophene수율 91.3%

시약·촉매·용매 3

HCID 10340Sodium Carbonate촉매HCID 178418397HCID 178418397, 화합물촉매2회HCID 80711,2-Dimethoxyethane용매

실험 절차

To a suspension of anhydrous 1,2-dimethoxyethane (DME, 20 mL) containing a palladium tetrakis catalyst (Pd(PPh3)4 (49.7 mg, 0.043 mmol) was added 4-iodonitrobenzene (535.8 mg, 2.15 mmol), stirred at room temperature for 10 minutes, followed by adding 4-methoxybenzothiophene-2-boronic acid (95a, 470 mg, 2.26 mmol) and 2.0 M sodium carbonate aqueous solution (43 mL, 0.086 mmol). The reaction mixture was heated to reflux for 10 hours and cooled to room temperature, and ice water was added. The resulting product was extracted with ethyl acetate, evaporated after a treatment with, and purified by column chromatograph to give the target compound 2-(4-nitrophenyl)-4-methoxybenzothiophene (1-1, 560 mg, 87%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 10 hours
  3. temperaturecooled to room temperature
  4. extractionThe resulting product was extracted with ethyl acetate
  5. customevaporated after a treatment with, and
  6. custompurified by column chromatograph

출처 및 근거

ORD 기록
ord-65192d248a6141eeae3e1a305b2f7d85
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497260B2

반응 노트

불러오는 중…