Chlorobenzene → 2-Methylbiphenyl

The general procedure from Example 13 was followed using chlorobenzene (1.126 g, 10.0 mmol) and o-tolylmagnesium chloride (15 mL, 15.0 mmol) with Ni(COD)2 (83.4 mg, 0.303 mmol) and (Me3C)2PH(O) (50.0 mg, 0.303 mmol) in 20.0 mL of THF. After 15 h at room temperature, the reaction mixture was quenched with 10 mL of H2O. The mixture above was extracted with 3×50 mL of diethyl ether. The combined ether extracts were dried over mgSO4, filtered, and the ether and THF removed from the filtrate by rotary evaporation. The resulting residues were chromatographed on silicon gel using ethyl acetate/hexane (5% volume ratio) as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to yield 1.62 g (96% yield) of 2-phenyltoluene. It was >95% pure by 1H NMR. 1H NMR (500 MHz, CDCl3): δ7.62-7.47 (m, 9H), 2.50 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ142.0, 141.9, 135.2, 130.3, 129.7, 129.1, 128.0, 127.2, 126.7, 125.7, 20.4. ppm.

1. customthe reaction mixture was quenched with 10 mL of H2O
2. extractionThe mixture above was extracted with 3×50 mL of diethyl ether
3. dry with materialThe combined ether extracts were dried over mgSO4
4. filtrationfiltered
5. customthe ether and THF removed from the filtrate by rotary evaporation
6. customThe resulting residues were chromatographed on silicon gel
7. concentrationThe eluate was concentrated by rotary evaporation

ORD record

ord-e934b01121c349f8814669da24b83498

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06762330B2