Potassium Carbonate → HCID 86628374, compound

HRID 553289Notes

Reaction equation

HRID 553289 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20](=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=1>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>[CH3:18][O:19][C:20](=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH:1]=[O:2])[CH:4]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 27343563-Formylphenylboronic acid

Product 1

HCID 86628374HCID 86628374, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

3-Formylphenylboronic acid (2.25 g), potassium carbonate (4.15 g) and tetrakis(triphenylphosphine)palladium(0) (0.58 g) was added to a solution of (4-bromophenyl)-acetic acid methyl ester (2.3 g) in a nitrogen degassed mixture of toluene and methanol [9:1] (20 mL) and heated to reflux for 18 hours. On cooling the reaction was filtered through a pad of Celite, the pad was washed with ethyl acetate (2×50 mL) and the combined filtrates were concentrated. Purification on silica, eluting with iso-hexane/ethyl acetate [1:0 to 4:1], afforded the subtitle compound as yellow oil (2.45 g)

Workup

  1. customdegassed
  2. additionmixture of toluene and methanol [9:1] (20 mL)
  3. temperatureheated
  4. temperatureto reflux for 18 hours
  5. temperatureOn cooling the reaction
  6. filtrationwas filtered through a pad of Celite
  7. washthe pad was washed with ethyl acetate (2×50 mL)
  8. concentrationthe combined filtrates were concentrated
  9. customPurification on silica
  10. washeluting with iso-hexane/ethyl acetate [1:0 to 4:1]

Sources & evidence

ORD record
ord-bc24bf60997b420b853d2b79e5106828
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

Loading…