Ethyl Acetate → 3'-Chloro-2-methoxy-1,1'-biphenyl

A suspension of 2-iodoanisol (3.00 g, 12.8 mmol), 3-chlorophenylboronic acid (2.41 g, 15.4 mmol), and potassium carbonate (3.54 g, 25.6 mmol) in water (10 mL) and methanol (50 mL) was purged with a nitrogen stream for 20 min. To the suspension was added palladium(II) acetate (57.6 mg, 0.2564 mmol) and the solution was stirred at room temperature overnight (18 h). To the reaction was added ethyl acetate (100 mL) and water (100 mL). The layers were separated, the aqueous layer extracted with ethyl acetate (100 mL), and the organic extracts were combined. The organic solution was washed with water (2×150 mL) and brine (150 mL), decolorized with activated charcoal, dried over sodium sulfate, and the solvent removed under reduced pressure. The resulting residue was purified by flash silica gel column chromatography eluting with 10-30% ethyl acetate in hexanes to give I-16 (2.50 g, 89% yield) as colorless oil. 1H NMR (400 MHz CDCl3) 7.53 (t, J=1.8 Hz, 1H), 7.40 (dt, J=7.2 Hz, 1.6 Hz, 1H), 7.38-7.28 (m, 4H), 7.05-6.97 (m, 2H), 3.82 (s, 3H).

1. customwas purged with a nitrogen stream for 20 min
2. customThe layers were separated
3. extractionthe aqueous layer extracted with ethyl acetate (100 mL)
4. washThe organic solution was washed with water (2×150 mL) and brine (150 mL)
5. dry with materialdried over sodium sulfate
6. customthe solvent removed under reduced pressure
7. customThe resulting residue was purified by flash silica gel column chromatography
8. washeluting with 10-30% ethyl acetate in hexanes
9. customto give I-16 (2.50 g, 89% yield) as colorless oil

ORD record

ord-dbdebdc29ce24c05a467198c17eb2a20

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791267B2