Sodium Chloride → 4'-Methyl-2-nitro-1,1'-biphenyl

Temperatur

110 °C

Under N2, a clean, dry flask was charged with p-tolyltrimethyltin (from Example 12, Step B) (5.61 g, 0.022 mol), 2-bromonitrobenzene (4.04 g, 0.020 mol), anhydrous DMF (40 mL), and palladium(II) bis(triphenylphosphine)dichloride (140 mg, 0.2 mmol), heated at 110° C. and stirred for 4 h when TLC (4:1 hexane/EtOAc) indicated disappearance of starting materials. The nearly black reaction mixture was cooled to room temperature, poured into a solution made from 100 mL 1N KOH and 100 mL sat. NaCl, and extracted with 3×150 mL EtOAc. The combined, organic layers were washed with 100 mL 1N KOH and 100 mL sat. NaCl, and then dried over anhydrous Na2SO4. After filtration, the amber solution was evaporated to dryness and then flash chromatographed over 900 mL SiO2, eluting with 2.5% EtOAc-hexane to give 4.109 g (96%) of the title compound as a light orange liquid, homogeneous on TLC (4/1 hex-EtOAc).

1. customUnder N2, a clean, dry flask
2. temperatureThe nearly black reaction mixture was cooled to room temperature
3. additionpoured into a solution
4. extractionextracted with 3×150 mL EtOAc
5. washorganic layers were washed with 100 mL 1N KOH and 100 mL sat. NaCl
6. dry with materialdried over anhydrous Na2SO4
7. filtrationAfter filtration
8. customthe amber solution was evaporated to dryness
9. customflash chromatographed over 900 mL SiO2
10. washeluting with 2.5% EtOAc-hexane

ORD-Eintrag

ord-441fb8a42a0440f9bb92c91ede0b45b0

Quelldatensatz

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05411980