Potassium Carbonate → 3-(3-Methoxy-5-nitro-phenyl)-thiophene

HRID 420362Notes

Reaction equation

HRID 420362 reaction equation
I[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([O:11][CH3:12])[CH:3]=1.[S:13]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.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>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([C:15]2[CH:16]=[CH:17][S:13][CH:14]=2)[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 106840391-Iodo-3-methoxy-5-nitrobenzene

Product 1

HCID 575864813-(3-Methoxy-5-nitro-phenyl)-thiopheneYield 92%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 1-iodo-3-methoxy-5-nitro-benzene (1.0 g, 3.59 mmol) in ethanol (18 mL) in a microwave tube were added tetrakis(triphenylphosphine)palladium(0) (837 mg, 0.72 mmol), thiophen-3-ylboronic acid (748 mg, 5.55 mmol), and potassium carbonate (496 mg, 3.58 mmol) at room temperature. The mixture was heated to 160° C. under closed microwave conditions for 30 minutes. After cooling to room temperature, the colored mixture was filtered and the filter cake was washed with water. The filtrate was diluted with 1.0 N HCl and the organic compound was extracted into ethyl acetate (2×50 mL). The combined organic extracts were washed with brine solution (100 mL) and dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified by using an ISCO 80 g column, eluting with 0-10% ethyl acetate in hexanes to obtain 3-(3-methoxy-5-nitro-phenyl)-thiophene (776 mg, 92%) as a light yellow oil: EI(+)-HRMS m/e calculated for C11H9NO3S (M+)+ 235.0303, found 235.0298.

Workup

  1. customunder closed microwave conditions for 30 minutes
  2. temperatureAfter cooling to room temperature
  3. filtrationthe colored mixture was filtered
  4. washthe filter cake was washed with water
  5. additionThe filtrate was diluted with 1.0 N HCl
  6. extractionthe organic compound was extracted into ethyl acetate (2×50 mL)
  7. washThe combined organic extracts were washed with brine solution (100 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude mixture was purified
  12. washeluting with 0-10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1f6c95efb5a84b83b48ce09bb43fe0e3
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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