Potassium Carbonate → 1-(2,2′-Dimethyl-5′-nitro[1,1′-biphenyl]-4-yl)-1-propanone

HRID 584322Notes

Reaction equation

HRID 584322 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[CH3:25].C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.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>[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[CH3:25]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 821892-Bromo-4-nitrotolueneHCID 22345627(2-Methyl-4-propanoylphenyl)boronic acid

Product 1

HCID 223456091-(2,2′-Dimethyl-5′-nitro[1,1′-biphenyl]-4-yl)-1-propanoneYield 81.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

2.5 g (13 mmol) of 2-methyl-4-propionylbenzeneboronic acid are placed in 100 ml of dimethoxyethane in a round-bottomed flask, and 2.2 g (10 mmol) of 2-bromo-4-nitrotoluene and 13 ml of aqueous 2M potassium carbonate solution are added. The medium is degassed for 10 minutes with a flow of nitrogen, and 580 mg (0.5 mmol) of tetrakis(triphenylphosphine)palladium are then added. The medium is stirred for 14 hours at 90° C. and then worked up as usual. The residue is obtained after chromatography on a column of silica (eluent: 1 ethyl acetate/9 heptane) to give 2.3 g (81%) of the expected product in the form of a yellow oil.

Workup

  1. additionare then added
  2. customThe residue is obtained after chromatography on a column of silica (eluent: 1 ethyl acetate/9 heptane)

Sources & evidence

ORD record
ord-ff71698e68a64e01b3e97c5251807d01
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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