Potassium Carbonate → HCID 58531509, compound

HRID 1889708Notes

Reaction equation

HRID 1889708 reaction equation
Br[C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cl:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=2[O:12][CH3:13])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 46311082Methyl 3-bromo-2-methoxybenzoate

Product 1

HCID 58531509HCID 58531509, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Methyl 3-bromo-2-methoxybenzoate (1.9 g, 7.75 mmol, 1.0 eq) was dissolved in toluene and treated with 4-chloro phenyl boronic acid (1.2 g, 7.75 mmol, 1 eq). The reaction mixture was stirred for 10 minutes, purged with nitrogen for 10 minutes and degassed with vacuum. Tetrakis triphenylphosphine palladium (0.447 g, 0.387 mmol, 0.05 eq) and K2CO3 (1.6 g, 11.62 mmol, 1.5 eq) were then added to the mixture. The mixture was heated to reflux for 12 h at 120° C. and cooled to ambient temperature. The solvents were evaporated under reduced pressure and the reaction mass was diluted with water. The aqueous mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by silica gel (60-120) column chromatography eluting with 5-10% ethyl acetate/hexane as the eluent to afford the desired product (1.7 g, 80%). 1H NMR (400 MHz, CDCl3) δ 3.49 (s, 3H), 3.93-3.95 (s, 3H), 7.20-7.25 (t, 1H), 7.39-7.53 (m, 5H), 7.74-7.78 (t, 1H). MS (ESI): 277.1 (M+H)+.

Workup

  1. custompurged with nitrogen for 10 minutes
  2. customdegassed with vacuum
  3. temperatureThe mixture was heated
  4. temperaturecooled to ambient temperature
  5. customThe solvents were evaporated under reduced pressure
  6. additionthe reaction mass was diluted with water
  7. extractionThe aqueous mixture was extracted with ethyl acetate
  8. dry with materialThe organic layer was dried with anhydrous Na2SO4
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by silica gel (60-120) column chromatography
  11. washeluting with 5-10% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-272e1e59da3543c794a9445e056bbe7d
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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