Ethyl Acetate → Ethyl 2'-cyano-2-methoxybiphenyl-4-carboxylate

HRID 519855Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1OS(C(F)(F)F)(=O)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O)#[N:23].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:13]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1])#[N:23]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of ethyl 3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate (7.0 g), (2-cyanophenyl)boronic acid (5.9 g), Pd(dppf)2Cl2 (0.50 g) and 2M aqueous cesium carbonate solution (20 mL) in tetrahydrofuran (60 mL) was stirred under an argon atmosphere at 70° C. for 3 hr. The mixture was allowed to cool, ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.28 g, 5%).

Workup

temperatureto cool
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-6bb531bd26254fcdb586e357759a38a5
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115136B2

Reaction notes

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