(4-Fluoro-2-methylphenyl)boronic acid → 3-(4-Methylthiophenyl)-4-(2-methyl-4-fluorophenyl)thiophene

HRID 1743895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743895
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[CH:13][S:14][CH:15]=2)=[CH:7][CH:6]=1)(=O)=O.[CH3:23]C1C=C(F)C=CC=1B(O)O>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][S:2][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=3[CH3:23])=[CH:13][S:14][CH:15]=2)=[CH:7][CH:6]=1

Komponenten

7

Edukt 2

HCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 104268843-(4-Methylsulfonylphenyl)-4-(4-fluorophenyl)thiophene

Produkt 1

HCID 545620343-(4-Methylthiophenyl)-4-(2-methyl-4-fluorophenyl)thiopheneAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

The mono-substituted thiophene from Example 14 (1.8 mmol, 520 mg) was combined with the 2-methyl-4-fluorophenyl boronic acid (2 eq, 3.6 mmol, 562 mg) in 8.0 ml of toluene, 4.3 ml of 2 M sodium carbonate, 10 ml of ethanol and tetrakis(triphenylphosphine)-palladium(0)(1.0 g) and was stirred at reflux overnight. The reaction was concentrated in vacuo and the residue was partitioned between toluene and water. The toluene layer was dried (MgSO4) and reconcentrated in vacuo. The residue was purified via silica chromatography (Waters, LC-2000) in 97% hexane/ethyl acetate to give 3-(4-methylthiophenyl)-4-(2-methyl-4-fluorophenyl)thiophene (420 mg) as a semi-solid. NMR (CDCl3) δ 1.90(s, 3H), 2.43(s, 3H), 6.8–6.9(m, 2H), 7.05(q, J=8 Hz, 4H), 7.12–7.18(m, 2H), 7.33(d, J=2 Hz, 1H).

Aufarbeitung

  1. temperatureat reflux overnight
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe residue was partitioned between toluene and water
  4. dry with materialThe toluene layer was dried (MgSO4)
  5. customThe residue was purified via silica chromatography (Waters, LC-2000) in 97% hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-49351749c2164a8e89e8fedbac5cfcbe
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012094B1

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