Sodium Carbonate → HCID 22326467, compound

HRID 495351Notes

Reaction equation

HRID 495351 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:14]2[O:13][CH:17]=[CH:16][CH:15]=2)[CH:6]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 2734357Furan-2-boronic acid

Product 1

HCID 22326467HCID 22326467, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of bromophenylacetic acid methyl ester (0.075 g, 0.328 mmol, 1.0 eq) in tetrahydrofuran (5.0 ml) was added 2-furanboronic acid (0.048 g, 0.426 mmol, 1.3 eq) and sodium carbonate (0.328 ml of a 2M soln in H2O). The solution was degassed and sonicated three times before adding tetrakis(triphenylphosphine)palladium (0.038 g, 0.033 mmol, 0.1 eq). The mixture was degassed and sonicated a further three times before stirring at 50° C. for 14 hours. After cooling to room temperature the solution was concentrated under reduced pressure. Column chromatography (silica, 20% EtOAc/hexane) yielded 3-furanylphenylacetic acid methyl ester (0.047 g, 67%) as a white solid; 1H-NMR (CDCl3, 400 MHz): δ 7.60 (1H, d, J=1.6 Hz), 7.47 (1H, t, J=1.0 Hz), 7.34 (1H, t, J=7.5 Hz), 7.19 (2H, m), 6.65 (1H, d, J=3.6 Hz), 6.48 (1H, dd, J=3.6, 1.6 Hz), 3.71 (3H, s), 3.66 (2H, s).

Workup

  1. customThe solution was degassed
  2. customsonicated three times
  3. customThe mixture was degassed
  4. customsonicated a further three times
  5. temperatureAfter cooling to room temperature the solution
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-e8d7231149414e5990011e628721478a
Source dataset
uspto-grants-2005_09
Patent number
US06939861B2

Reaction notes

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