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

HRID 454801Notes

Reaction equation

HRID 454801 reaction equation
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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 10340Sodium CarbonateCatalystHCID 178418397HCID 178418397, compoundCatalyst2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-65192d248a6141eeae3e1a305b2f7d85
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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