Acetone → 2-Methyl-5-nitrobiphenyl

HRID 1739152Notes

Reaction equation

HRID 1739152 reaction equation
CC(C)=O.Br[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[CH3:15].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[N+:12]([C:10]1[CH:9]=[CH:8][C:7]([CH3:15])=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=1)([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 821892-Bromo-4-nitrotoluene

Product 1

HCID 107510832-Methyl-5-nitrobiphenylYield 88.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

To a mixture of 70 mL of acetone and 85 mL of water was added 2-bromo-4-nitrotoluene 6.84 g (30 mmol), phenylboronic acid 3.84 g (31.5 mmol), potassium carbonate 10.35 g (75 mmol) and palladium acetate 336 mg (1.5 mmol). The mixture was refluxed for 10 hr and then extracted with ether and dilute hydrochloric acid. After evaporating solvents, the solid residue was recrystallized from methanol to give 5.64 g of 4-nitro-2-phenyltoluene (88% yield). 1H NMR (CDCl3) δ 8.09-8.11 (m, 2H), 7.40-7.49 (m, 4H), 7.30-7.33 (m, 2H), 2.37 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 10 hr
  2. extractionextracted with ether and dilute hydrochloric acid
  3. customAfter evaporating solvents
  4. customthe solid residue was recrystallized from methanol

Sources & evidence

ORD record
ord-d403736173694bf3a00cd9ac38702cf1
Source dataset
uspto-grants-1999_10
Patent number
US05965539

Reaction notes

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