Diethyl Ether → 2-Methoxy-3-(propan-2-yl)-1,1'-biphenyl

HRID 658226Notes

Reaction equation

HRID 658226 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8](C)C)[C:3]=1OC.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+].[CH2:32]([O:34][CH2:35][CH3:36])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(COC)OC.O>[CH:4]([C:3]1[CH:2]=[CH:7][CH:6]=[C:36]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:35]=1[O:34][CH3:32])([CH3:8])[CH3:5]

Participants

10

Reactant 5

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 113336702-bromo-6-isopropylanisol

Product 1

HCID 224043852-Methoxy-3-(propan-2-yl)-1,1'-biphenyl

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1.98 g (8.64 mmol) of 2-bromo-6-isopropylanisol, 2.10 g (17.28 mmol) of phenylboronic acid, 96 mg (0.43 mmol) of palladium acetate, 0.225 g (0.86 mmol) of triphenylphosphine and 11 g (51.84 mmol) of potassium phosphate were placed in a flask, and a mixed solution of 8 ml of water and 32 ml of dimethoxyethane was added thereto. The mixture was refluxed at room temperature for 12 hours. After the refluxed solution was cooled to room temperature, 15 ml of an aqueous ammonium chloride solution and 30 ml of diethyl ether were added thereto. Then, the organic layer was separated and the residue was extracted with diethyl ether. The collected organic layer was dried over magnesium sulfate, and volatile materials were removed therefrom, thus obtaining 2 g of 2-isopropyl-6-phenylanisol as a gray solid. The obtained anisol was dissolved in 15 ml of methylene chloride without a separate purification process, and then 12 ml of boron tribromide (1M methylene chloride) was added dropwise thereto at −78° C., and the mixture was warmed slowly to room temperature and allowed to react for 12 hours. After completion of the reaction, a mixed solution of 15 ml of water and 30 ml of diethyl ether was added thereto. The organic layer was separated and the aqueous layer was extracted with diethyl ether (15 ml×3). The collected organic layer was dried, and volatile components were removed in a vacuum. The residue was purified using a silica gel chromatography column in a mixed solvent of hexane and methylene chloride, thus obtaining 1.72 g of 2-isopropyl-6-phenylphenol as a white solid.

Workup

  1. temperatureAfter the refluxed solution was cooled to room temperature
  2. customThen, the organic layer was separated
  3. extractionthe residue was extracted with diethyl ether
  4. dry with materialThe collected organic layer was dried over magnesium sulfate, and volatile materials
  5. customwere removed

Sources & evidence

ORD record
ord-5c967c27d8bc49f4a5c225def4f885f1
Source dataset
uspto-grants-2011_12
Patent number
US08076428B2

Reaction notes

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