Cyclohexane → 4-Methyl-3-nitro-1,1'-biphenyl

Phenyllithium (10 ml of a 2.0M solution in a 7:3 mixture of cyclohexane and ether, 20 mmol) was added dropwise to zinc chloride (20 ml of a 1.0M solution in ether, 20 mmol) at room temperature. The resulting mixture was stirred for 2 hours, then a solution of 4-iodo-2-nitrotoluene (2.63 g, 10 mmol) in THF (20 ml) and tetrakis(triphenylphosphine)palladium (0.3 g, 0.26 mmol) were added successively. The reaction mixture was stirred for 3 hours then diluted with 0.5M hydrochloric acid (40 ml) and extracted with ether (3×70 ml). The ether extracts were washed with brine, dried, concentrated then purified by column chromatography using petrol (60°-80° C.)-ethyl acetate (9:1) on silica gel to give 4-phenyl-2-nitrotoluene (1.8 g, 85% yield) as a yellow oil.

1. stirringThe reaction mixture was stirred for 3 hours
2. extractionextracted with ether (3×70 ml)
3. washThe ether extracts were washed with brine
4. customdried
5. concentrationconcentrated
6. customthen purified by column chromatography
7. custompetrol (60°-80° C.)-ethyl acetate (9:1)

ORD-Eintrag

ord-4776b8af320a493f9e61978559b649b3

Quelldatensatz

uspto-grants-1989_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04812162