1,4-Dioxane → Methyl 2'-cyano-5-hydroxy-4'-methylbiphenyl-3-carboxylate

HRID 1845280Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5](B2OC(C)(C)C(C)(C)O2)=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:19][O:20][C:21](=[O:30])[C:22]1[CH:27]=[C:26]([OH:28])[CH:25]=[C:24](Br)[CH:23]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:7]([C:6]1[CH:9]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[C:24]1[CH:25]=[C:26]([OH:28])[CH:27]=[C:22]([C:21]([O:20][CH3:19])=[O:30])[CH:23]=1)#[N:8]

Participants

Conditions

Temperature: 85 °C

Procedure

Under an atmosphere of nitrogen, a flask was charged with 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (2.1 g, 8.2 mmol), 3-bromo-5-hydroxy-benzoic acid methyl ester (1.5 g, 6.2 mmol), potassium phosphate (2.8 g, 13 mmol), tetrakis(triphenylphosphine)palladium(0) (400 mg, 0.35 mmol), 1,4-dioxane (90 mL), and water (20 mL). The reaction mixture was stirred at 85° C. overnight. After cooling, the mixture was filtered through Celite and the filter cake was washed with EtOAc. The filtrate was concentrated and the residue was purified by silica gel column to afford the title compound.

Workup

temperatureAfter cooling
filtrationthe mixture was filtered through Celite
washthe filter cake was washed with EtOAc
concentrationThe filtrate was concentrated
customthe residue was purified by silica gel column

Sources & evidence

ORD record: ord-77e2ab37c06046a48d864f8f54655b41
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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