Sodium Carbonate → 2-Methyl-4-nitro-1-phenylbenzene

HRID 1701008Notes

Reaction equation

HRID 1701008 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH3:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 2516721-Bromo-2-methyl-4-nitrobenzene

Product 1

HCID 143174152-Methyl-4-nitro-1-phenylbenzeneYield 86%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

According to the method of Preparation 25(a), 2-bromo-5-nitrotoluene (15 gm, 69.4 mmol) was treated with phenyl boronic acid (12.7 gm, 104.1 mmol) under palladium catalysis, using 2M aqueous sodium carbonate as base at reflux in dimethoxyethane for 16 h. After being cooled, the mixture was separated the organic layer was diluted with diethyl ether and washed with water (twice). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane to hexane:ethyl acetate 95:5) to give 2-methyl-4-nitro-1-phenylbenzene as a yellow solid (12.7gm, 86%).

Workup

  1. temperatureAfter being cooled
  2. customthe mixture was separated the organic layer
  3. additionwas diluted with diethyl ether
  4. washwashed with water (twice)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (gradient elution with hexane to hexane:ethyl acetate 95:5)

Sources & evidence

ORD record
ord-36a908b520c4492abae4c820bdc7ebd4
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

Loading…