Potassium Phosphate, Tribasic → 4-Methyl-3-nitro-1,1'-biphenyl

HRID 912381Notes

Reaction equation

HRID 912381 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CN(C=O)C>[CH3:11][C:4]1[CH:3]=[CH:2][C:7]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 2

HCID 62657Potassium Phosphate, TribasicHCID 815772-Bromo-5-nitrotoluene

Product 1

HCID 129098264-Methyl-3-nitro-1,1'-biphenylYield 185.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a DMF solution (5.0 ml) of 4-bromo-2-methyl-1-nitro-benzene (500 mg), palladium acetate (10.4 mg), S-Phos (38.0 mg) and potassium phosphate (983 mg), phenylboronic acid-pinacol ester (496 mg) was added, and then the mixture was degassed under ultrasonic irradiation. After the mixture was stirred at 100° C. for 18 hours, water (20 ml) was added, followed by extraction with ethyl acetate (20 ml×2), and the organic layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography (hexane/ethyl acetate=100/1), to obtain the desired compound (457 mg, 93%).

Workup

  1. customthe mixture was degassed under ultrasonic irradiation
  2. additionwater (20 ml) was added
  3. extractionfollowed by extraction with ethyl acetate (20 ml×2)
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationAfter the sodium sulfate was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customfollowed by purification by silica gel column chromatography (hexane/ethyl acetate=100/1)

Sources & evidence

ORD record
ord-865d8174ed804dada130866b4b33ce92
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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