Potassium Phosphate, Tribasic → Methyl 4'-(2-ethoxyethoxy)-6-methoxy-2',6'-dimethylbiphenyl-3-carboxylate

HRID 273386Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[CH2:14]([O:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23](B(O)O)=[C:22]([CH3:30])[CH:21]=1)[CH3:15].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH2:14]([O:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[C:22]([CH3:30])[C:23]([C:2]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)=[C:24]([CH3:26])[CH:25]=1)[CH3:15]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of methyl 3-bromo-4-methoxybenzoate (0.90 g, 3.67 mmol), [4-(2-ethoxyethoxy)-2,6-dimethylphenyl]boronic acid (0.87 g, 3.67 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.13 g, 0.15 mmol), 2-(dicyclohexylphosphino)biphenyl (79 mg, 0.22 mmol), tripotassium phosphate (1.56 g, 7.34 mmol) and toluene (20 mL) was stirred under a nitrogen atmosphere at 90° C. for 18 hrs. The reaction mixture was cooled and insoluble material was filtered off. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1) to give the title compound (0.71 g, yield 54%) as a yellow oil.

Workup

temperatureThe reaction mixture was cooled
filtrationinsoluble material was filtered off
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-12fe0048171945cd8cee2856ddbdce3a
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456218B2

Reaction notes

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