Potassium Carbonate → HCID 18680371, compound

HRID 1755072Notes

Reaction equation

HRID 1755072 reaction equation
B([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Br[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:40]1([C:45]2[C:50]([C:4]3[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=3)=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:41]=[CH:42][CH:43]=[CH:44][CH:39]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 163292-BromobiphenylHCID 27339573-Carboxyphenylboronic acid

Product 1

HCID 18680371HCID 18680371, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

3-Boronobenzoic acid (300 mg, 1.81 mmol), palladium acetate (40.4 mg, 0.18 mmol), triphenylphosphine (94.6 mg, 0.36 mmol) and potassium carbonate (374.6 mg, 2.71 mmol) were added to a solution of 2-bromo-1,1′-biphenyl (0.3 ml, 1.81 mmol) in acetonitrile (10 mL)-water (2.5 ml), and the mixture was heated with stirring at 100° C. overnight. The reaction mixture was cooled and then filtered through celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give [1,1′;2′,1″]terphenyl-3″-carboxylic acid (191 mg, 39%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-11ae1bf9a1a94fbdb48e45f699c94d67
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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