Sodium Carbonate → Methyl 4-[4-(4-pentoxyphenyl)phenyl]benzoate

HRID 1884214Notes

Reaction equation

HRID 1884214 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:18]([O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)[CH2:19][CH2:20][CH2:21][CH3:22].C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[CH2:18]([O:23][C:24]1[CH:25]=[CH:26][C:27]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:28][CH:29]=1)[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1394054Methyl 4'-iodo-[1,1'-biphenyl]-4-carboxylateHCID 46848884-Pentyloxyphenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 9799723Methyl 4-[4-(4-pentoxyphenyl)phenyl]benzoate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

33.8 g (0.1 mol) of methyl 4′-iodobiphenyl-4-carboxylate are introduced together with 29.3 g (0.125 mol) of glycol ester of 4-n-pentoxyphenylboronic acid, 70 mg of bis(triphenylphosphine)palladium dichloride and 15.9 g (0.15 mol) of sodium carbonate into 300 ml of DMF and stirred at 80° C. for 12 hours. After filtration and washing with water, the dried residue is recrystallized from DMF. This affords 20.5 g (45%) of methyl 4″-n-pentoxy-[1,1′:4′,1″]-terphenyl-4-carboxylate of melting point 248° C.

Workup

  1. filtrationAfter filtration
  2. washwashing with water
  3. customthe dried residue is recrystallized from DMF

Sources & evidence

ORD record
ord-ce48e19a42ff472baded19bebc663d84
Source dataset
uspto-grants-2004_07
Patent number
US06762315B1

Reaction notes

Loading…