Triethylamine → HCID 67342987, compound

HRID 2191638Notes

Reaction equation

CN(C)C(=O)C.Br[C:8]1[CH:20]=[CH:19][C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=1.[CH:24]([C:26]1[CH:27]=[C:28]([O:32][CH3:33])[CH:29]=[CH:30][CH:31]=1)=[CH2:25].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C>[CH3:33][O:32][C:28]1[CH:27]=[C:26](/[CH:24]=[CH:25]/[C:8]2[CH:20]=[CH:19][C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=2)[CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To N,N-dimethylacetamide 5 mL solution of tert-butyl 4-bromo-2-nitrobenzoate 0.50 g were added 3-vinylanisole 0.37 mL, triethylamine 0.47 mL and palladium acetate 0.11 g at room temperature, and it was stirred under nitrogen atmosphere at 110° C. for 4 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=10:1] to give tert-butyl 4-((E)-2-(3-methoxyphenyl)vinyl)-2-nitrobenzoate 0.20 g of pale yellow solid.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customThe organic layer was separated
washafter sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-ef1d216e46a946079d56f3718c0b952a
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08327467B2

Reaction notes

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