Sodium Carbonate → Methyl 3,5-bis[(1E)-3-methoxyprop-1-en-1-yl]benzoate

HRID 658248

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10](Br)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][O:14][CH2:15]/[CH:16]=[CH:17]/B1OC(C)(C)C(C)(C)O1.[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:32]=CC=C[CH:28]=1.[C:46](=O)([O-])[O-:47].[Na+].[Na+]>CN(C=O)C.CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:46][O:47][CH2:28]/[CH:27]=[CH:32]/[C:2]1[CH:3]=[C:4]([CH:9]=[C:10](/[CH:17]=[CH:16]/[CH2:15][O:14][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 3,5-dibromobenzoate (1 eq.) from the previous step in DMF (0.2 M) was added 2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.1 eq.), palladium acetate (10 mol %), triphenylphosphine (30 mol %), and 2.0 M aqueous sodium carbonate solution (5 eq.). The reaction was heated to 80° C. and stirred for 3 h. After cooling to rt, the reaction was diluted with ether. The organic extract was washed with water, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex) to afford the title compound as an oil.

Workup

temperatureAfter cooling to rt
extractionThe organic extract
washwas washed with water, brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex)

Sources & evidence

ORD record: ord-d53dca1151d34266a90db378e16b3d56
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076359B2

Linked notes

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