Chlorobenzene → 4-Methylbiphenyl

A 100 mL of reactor equipped with magnetic stir bar was charged with 102 mg (0.15 mmol) of {[(t-Bu)2P(OH)]PdCl2}2 (from Experiment 7), 1.13 g (10.0 mmol) of chlorobenzene, 2.04 g (15.0 mmol) of MeC6H4B(OH)2 and 4.56 g (30.0 mmol) of CsF in 30.0 mL of 1,4-dioxane. The resulting mixture was refluxed for 15 h until the starting material was completely consumed as judged by TLC. The reaction was cooled to room temperature, transferred to a separatory funnel, and diluted with 300 mL of hexane. The layers were separated, and organic layer was washed with H2O (2×100 mL), brine (100 mL), and dried over mgSO4, filtered, and the hexane and dioxane removed from the filtrate by rotary evaporation. The resulting residue was chromatographed on silicon gel using hexane as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to give 1.58 g (94% yield) of 4-phenyltoluene.

1. customA 100 mL of reactor equipped with magnetic stir bar
2. temperatureThe resulting mixture was refluxed for 15 h until the starting material
3. customwas completely consumed
4. customtransferred to a separatory funnel
5. additiondiluted with 300 mL of hexane
6. customThe layers were separated
7. washorganic layer was washed with H2O (2×100 mL), brine (100 mL)
8. customdried over mgSO4
9. filtrationfiltered
10. customthe hexane and dioxane removed from the filtrate by rotary evaporation
11. customThe resulting residue was chromatographed on silicon gel
12. concentrationThe eluate was concentrated by rotary evaporation

ORD record

ord-c6825456021f401cba53f44900f72e5a

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06762330B2