Potassium Carbonate → HCID 14923755, compound

HRID 514750Notes

Reaction equation

HRID 514750 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-94b651c95aff4dcd9a643a11ec9be93b
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Reaction notes

Loading…