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Home > Encyclopedia > 2-(4-Bromophenyl)-5-phenylthiophene

2-(4-Bromophenyl)-5-phenylthiophene

2-(4-Bromophenyl)-5-phenylthiophene structure
  • CAS No:

    118621-30-0

  • Formula:

    C16H11BrS

  • Synonyms:

    2-(4-bromophenyl)-5-phenylthiophene;2-(4-Bromophenyl)-5-phenyl thiophene;SCHEMBL10041710;KS-00000LPL;MFCD21648452;ZINC38482281;2-Phenyl-5-(4-bromophenyl)thiophene;Thiophene,2-(4-bromophenyl)-5-phenyl-;AK402301;DA-17134

  • Categories:

    Pharmaceutical Intermediates  >  Oled Material Intermediate

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Basic Attributes

  • 118621-30-0

  • C16H11BrS

  • 315.22754

  • 313.976471

  • 28.2

  • 5.6

  • YMDCOEOZWHXGTM-UHFFFAOYSA-N

  • 1

  • 0

  • 0.00

  • 2

Characteristics

  • 1.396

  • 189.0 to 193.0 °C

  • 409.7±30.0 °C(Predicted)

  • 201.6±24.6 °C

  • 1.642

Safety Information

Production Methods

20.4 g (100 mmol, 1.0 eq.) of 5-phenyl-2-thiophenolboronic acid and 31.1 g (110 mmol, 1.1 eq.) of p-bromoiodobenzene were added to a 2 L three-necked flask and 1000 ml of toluene and 100 ml of ethanol were added. Dissolve, purge with nitrogen for 15 minutes, add 150 ml of 2M aqueous solution containing 41.5 g (300 mmol, 3.0 eq.) of K2CO3, and finally add 2.3 g of Pd(PPh3)4 (2 molpercent). The temperature was raised to 110°C and the reaction was completed overnight. Activated carbon adsorption was added, suction filtration, solvent removal, drying and recrystallization from toluene and ethanol gave 26.2 g of intermediate-9 with a yield of 83percent.20.4 g (100 mmol, 1.0 eq.) of 5-phenyl-2-thiophene boric acid and 31.1 g (110 mmol, 1.1 eq.)P-bromo-iodobenzene was added to a 2L three-necked flask was charged with 1000ml of toluene and 100ml of ethanol were dissolved, After nitrogen was passed for 15 minutes, 150 ml of a 2M aqueous solution containing 41.5 g (300 mmol, 3.0 eq.) of K2CO3 was added, and finally 2.3 g of Pd(PPh3)4 (2 mol percent) was added.The temperature was raised to 100°C and the reaction ended overnight. Add activated carbon adsorption, suction filtration, remove the solvent, It was dried and recrystallized from toluene and ethanol to give 19.6 g of Intermediate-17 with a yield of 78percent.2-Thiophene boronic acid (10 g, 78.1 mmol) and bromo benzene (7.48 mL, 70.3 mmol) were dissolved in anhydrous THF (300 mL), and then Pd(PPh ) (4.51 g, 3.913 4 mmol) and a K CO aqueous solution (156 mL, 312.4 mmol) were added thereto, 2 3 refluxed for 3 hrs. The organic layer was extracted with ethyl acetate, and dried over magnesium sulfate. The organic layer was filtered under reduced pressure, and concentrated to remove the solvent. The residue was purified by column chromatography, and then recrystallized in THF and ethanol to obtain a white solid compound (1O g, 83percent).[125] MS: [M+H] = 161.[126] The prepared white solid compound (5 g, 31.3 mmol) were dissolved in anhydrous THF (200 mL), and then cooled to -1OAfter 1-bromo-4-iodobenzene (2.82 g, 10 mmol) and 2-phenyl-cyophenboronic acid (2.04 g, 10 mmol) were dissolved in tetrahydrofuran (30 mL), 2M potassium carbonate aqueous solution (20 mL) was added thereto, and tetrakistriphenylphosphino palladium (Pd(PPh1-bromo-4-iodobenzene (2.82g, 10mmol) and 2-phenyl-5-thiophenyl boronic acid (2.04g, 10mmol) were dissolved in THF (30mL), 2M K2CO3 aqueous solution (20mL) was added, Pd (PPh3)4 (0.231g, 2molpercent) was added and stirred under reflux for 5 hours. The reaction mixture was cooled to room temperature, aqueous layer was removed, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The solution was filtered, concentrated under reduced pressure, and recrystallized with ethyl ether to obtain compound B-17(2.2g, 70percent yield).

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