ChemicalBook CAS DataBase List 1,1'-Biphenyl, 4'-bromo-2,4,6-trimethyl-

1,1'-Biphenyl, 4'-bromo-2,4,6-trimethyl- synthesis

6synthesis methods

Product Name:1,1'-Biphenyl, 4'-bromo-2,4,6-trimethyl-
CAS Number:20434-38-2
Molecular formula:C15H15Br
Molecular Weight:275.18

589-87-7 Synthesis

589-87-7
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5980-97-2 Synthesis

5980-97-2
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1,1'-Biphenyl, 4'-bromo-2,4,6-trimethyl-

20434-38-2
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Yield:20434-38-2 86%

Reaction Conditions:

with barium dihydroxide;tetrakis(triphenylphosphine) palladium⁽⁰⁾ in 1,4-dioxane;water; for 22 h;Heating / reflux;

Steps:

20 Synthesis of 4-Bromo-2',4',6'-trimethylbiphenyl (GA35)

GA33 (4.98 mmol) obtained in Synthetic example 19, barium hydroxide octahydrate (14.9 mmol), Pd(PPh₃)₄ (0.24 mmol), degassed dioxane (33 mL), and distillated water (11 mL) were put in a three-necked round bottom flask and stirred. To the solution, GA31 (15.0 mmol) obtained in Synthetic example 18 was added, and the reaction mixture was heated and refluxed for 22 hours. The reaction mixture was cooled to room temperature. Dioxane was distilled away under a reduced pressure. After addition of 1 M hydrochloric acid, the mixture was extracted with dichloromethane three times. The combined extracts was washed with 1 M hydrochloric acid twice and with brine once, and dried over anhydrous sodium sulfate. After the drying, the extract was filtered. By means of column chromatography, the obtained solid was firstly separated with Hexane:CH₂Cl₂=2:1, and then separated and purified with Hexane:CH₂Cl₂=1:1 to give GA35 (11.50 mmol, yield: 86%). Rf=0.6. ¹H-NMR(400MHz,CDCl₃) δ = 7.52(d,2H,J=8.2Hz), 7.00(d,2H,J=8.2Hz), 6.92(s,2H), 2.31(s,3H), 1.98(s,6H). ¹³C-NMR(100MHz,CDCl₃) δ = 139.95, 137.66, 136.89, 135.74, 131.56, 131.07, 128.13, 120.60, 20.99, 20.68.