Hydrogen Peroxide → 4-Methoxy-2,6-dimethyl-1,1'-biphenyl

HRID 414613Notes

Reaction equation

HRID 414613 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[C:4]([CH3:9])[C:3]=1OC.[C:12]1(OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.OO.[OH2:24].[C:25]1(C)C=CC=CC=1>C(=O)([O-])[O-].[Na+].[Na+].C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([O:24][CH3:25])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 1140TolueneHCID 78412Phenyl dihydrogen orthoborate2×HCID 2786544-Bromo-2,6-dimethylanisole

Product 1

HCID 135430144-Methoxy-2,6-dimethyl-1,1'-biphenyl

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent2×HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 2,6-dimethyl-4-bromoanisole (4.14 g) and tetrakis (triphenylphosphine) palladium (0.69 g) in toluene (40 ml) and 2.0 molar aqueous sodium carbonate (20 ml) was added phenylboric acid (2. 7 g) in ethanol (10 ml). The reaction was heated at reflux for 16 hours, at which time a solution of phenylboric acid (1.0 g) in ethanol (3 ml) was added. The reaction was heated at reflux for a further 6 hours and then cooled to 25° C., and 30% hydrogen peroxide (1.0 ml) was added. The mixture was stirred for one hour, then poured into water and extracted with ether. The organic phase was dried and evaporated and the residue was chromatographed on silica gel, eluting with 9:1 hexane either, so as to afford 2,6-dimethyl-4-methoxybiphenyl.

Workup

  1. temperatureThe reaction was heated
  2. additionwas added
  3. temperatureThe reaction was heated
  4. temperatureat reflux for a further 6 hours
  5. extractionextracted with ether
  6. customThe organic phase was dried
  7. customevaporated
  8. customthe residue was chromatographed on silica gel
  9. washeluting with 9:1 hexane either

Sources & evidence

ORD record
ord-6f15d887dd234096acc310fa9d4ca08d
Source dataset
uspto-grants-1988_12
Patent number
US04792570

Reaction notes

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