4-Chloroanisole → 4-Methoxybiphenyl

A 100 mL of reactor equipped with magnetic stir bar was charged with 140 mg (0.15 mmol) of {[(t-Bu)2P(OH)]2PdCl}2 (from Experiment 7), 1.43 g (10.0 mmol) of 4-chloroanisole, 1.83 g (15.0 mmol) of PhB(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 8 h until the starting material was completely consumed as judged by GC. The reaction was cooled to room temperature, transferred to a separatory funnel, and diluted with 300 mL of diethyl ether and 100 mL of H2O. The layers were separated, and organic layer was washed with H2O (2×100 mL), brine (100 mL), and dried over mgSO4, filtered, and the ether and dioxane removed from the filtrate by rotary evaporation. The resulting residue was chromatographed on silicon gel using 2% EtOAc/hexane as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to give 0.97 g (53% yield) of 4-phenylanisole.

1. customA 100 mL of reactor equipped with magnetic stir bar
2. temperatureThe resulting mixture was refluxed for 8 h until the starting material
3. customwas completely consumed
4. customtransferred to a separatory funnel
5. additiondiluted with 300 mL of diethyl ether and 100 mL of H2O
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 ether 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-99b89c1da127425ba0fb0d2468611754

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06762330B2