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

HRID 658248
Notes
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Reaction equation

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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 621923Methyl 3,5-DibromobenzoateHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 57456870Methyl 3,5-bis[(1E)-3-methoxyprop-1-en-1-yl]benzoate

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
HCID 3283Diethyl EtherSolvent
HCID 6228DimethylformamideSolvent

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

  1. temperatureAfter cooling to rt
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes