Ethyl Acetate → 2-Fluoro-4-methoxy-1-(2-methylphenyl)benzene

HRID 2093133Notes

Reaction equation

HRID 2093133 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[F:10].[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O>O.CCO.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCCCCC>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH3:11])=[C:3]([F:10])[CH:4]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 37184441-Bromo-2-fluoro-4-methoxybenzene

Product 1

HCID 670659662-Fluoro-4-methoxy-1-(2-methylphenyl)benzene

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8058HexaneSolventHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of 4-bromo-3-fluoroanisole, 2-methylphenyl boronic acid, tetrakis(triphenylphosphine)palladium (5% mol) and sodium carbonate (0.23 g, 2.1 mmol) in 20 ml of water/EtOH/toluene (1:2:4) was heated to reflux for 5 h. TLC (EtOAc:hexane/2:98) showed that the reaction was over. The solvents was removed. Water (10 ml) was added. The organic was extracted with methylene chloride (3×50 ml). The combined methylene chloride layers were washed with brine, and dried over sodium sulfate. The title compound was obtained after purification with preparative TLC using 2% EtOAc in hexane as the eluant.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. customThe solvents was removed
  4. additionWater (10 ml) was added
  5. extractionThe organic was extracted with methylene chloride (3×50 ml)
  6. washThe combined methylene chloride layers were washed with brine
  7. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-ad1e7153c9604834970515733d644cd0
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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