Potassium Carbonate → 1-Isopropenyl-4,5-dimethoxy-2-nitro-benzene

HRID 1691844Notes

Reaction equation

HRID 1691844 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].[C:21](B1OC(C)(C)C(C)(C)O1)([CH3:23])=[CH2:22]>O1CCOCC1.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>[C:21]([C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])([CH3:23])=[CH2:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1709684-Bromo-5-nitroveratroleHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane

Product 1

HCID 593778431-Isopropenyl-4,5-dimethoxy-2-nitro-benzeneYield 28.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1-Bromo-4,5-dimethoxy-2-nitro-benzene (6.55 g, 25.0 mmol), potassium carbonate (2 eq, 6.91 g) and tetrakis(triphenylphosphine)palladium(0) (0.125 eq, 3.61 g) were dissolved in dioxane. Isopropenylboronic acid pinacol ester (1 eq, 4.7 ml) was added and the mixture was heated to 100° C. overnight. Upon cooling the mixture was filtered through celite. The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography (gradient 9:1 to 1:1 Hexanes/Ethyl Acetate) to give 1-isopropenyl-4,5-dimethoxy-2-nitro-benzene (1.59 g, 28.5%) as a yellow oil.

Workup

  1. temperatureUpon cooling the mixture
  2. filtrationwas filtered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography (gradient 9:1 to 1:1 Hexanes/Ethyl Acetate)

Sources & evidence

ORD record
ord-8a05b740cc2140619e5aff7f443c6dcb
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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