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

HRID 454801ノート

反応式

HRID 454801 の反応式
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]

参加物

6

反応物 2

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

生成物 1

HCID 469469612-(4-Nitrophenyl)-4-methoxybenzothiophene収率 91.3%

試薬・触媒・溶媒 3

HCID 10340Sodium Carbonate触媒HCID 178418397HCID 178418397、化合物触媒2 回HCID 80711,2-Dimethoxyethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-65192d248a6141eeae3e1a305b2f7d85
出典データセット
uspto-grants-2013_07
特許番号
US08497260B2

反応ノート

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