Potassium Carbonate → HCID 14923755, compound

HRID 1614997Notes

Reaction equation

HRID 1614997 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Cl[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22].C([O-])([O-])=O.[K+].[K+].CCCCCC.C(OCC)(=O)C>O1CCOCC1.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>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[C:14]([N+:21]([O-:23])=[O:22])[CH:15]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 251404-Chloro-3-nitroanisoleHCID 201262(4-Methoxyphenyl)boronic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 14923755HCID 14923755, compoundYield 199.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

4-Methoxyphenylboronic acid (3.00 g, 19.7 mmol) and 4-chloro-3-nitroanisole (3.69 g, 11.6 mmol) were dissolved in a mixture of dioxane (40 mL) and water (10 mL). K2CO3 (5.44 g, 23.2 mmol) and Pd(PPh3)4 (1.14 g, 0.6 mmol) were added. The reaction mixture was heated in argon to 80° C., kept at this temperature overnight (TLC monitoring: hexane/ethyl acetate, 4:1), cooled, and filtered through Celite. The latter was washed with CH2Cl2, and the filtrate was evaporated. The residue was dissolved in CH2Cl2, and the solution was evaporated to give 6.0 g of crude biphenyl 10h that was cyclized without purification.

Workup

  1. temperaturecooled
  2. filtrationfiltered through Celite
  3. washThe latter was washed with CH2Cl2
  4. customthe filtrate was evaporated
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. customthe solution was evaporated

Sources & evidence

ORD record
ord-16bd4e95711e4e88a591137c91768501
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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