Sodium Carbonate → 158938-08-0 4-N-Pentoxyterphenyl-carbonic acid

HRID 1884211Notes

Reaction equation

HRID 1884211 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:23]([O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)[CH2:24][CH2:25][CH2:26][CH3:27]>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.CS(C)=O>[CH2:23]([O:28][C:29]1[CH:30]=[CH:31][C:32]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:33][CH:34]=1)[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 8167304'-Iodobiphenyl-4-carboxylic acidHCID 46848884-Pentyloxyphenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 9798987158938-08-0 4-N-Pentoxyterphenyl-carbonic acid

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
105 °C

Procedure

20.1 g of 4′-iodobiphenyl-4-carboxylic acid, 13.1 g of sodium carbonate and 21.4 g of glycol ester of 4-n-pentoxyphenylboronic acid are introduced into 260 g of dimethyl sulfoxide (DMSO) and, after addition of 160 mg of PdCl2(PPh3)2, heated at 100-110° C. for 2 hours. The solid is filtered off at 40° C., washed with dimethyl sulfoxide and suspended in 100 ml of water. It is then heated to 80° C., and 47 g of 37% strength sulfuric acid are added dropwise over the course of 1 hour. The mixture is stirred at 80° C. for a further 30 minutes, cooled at 40° C. and filtered. Drying and crystallization from dimethylacetamide results in 18 g (81%) of 4″-n-pentoxy-[1,1′:4′,1″]-terphenyl-4-carboxylic acid with a purity of >99%.

Workup

  1. filtrationThe solid is filtered off at 40° C.
  2. washwashed with dimethyl sulfoxide
  3. temperatureIt is then heated to 80° C.
  4. addition47 g of 37% strength sulfuric acid are added dropwise over the course of 1 hour
  5. temperaturecooled at 40° C.
  6. filtrationfiltered
  7. customDrying
  8. customcrystallization from dimethylacetamide
  9. customresults in 18 g (81%) of 4″-n-pentoxy-[1,1′:4′,1″]-terphenyl-4-carboxylic acid with a purity of >99%

Sources & evidence

ORD record
ord-2b67392bf75f40dfb0fb377f2a70c102
Source dataset
uspto-grants-2004_07
Patent number
US06762315B1

Reaction notes

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