Tetrahydrofuran → Methyl (2'-fluoro[1,1'-biphenyl]-4-yl)acetate

HRID 1362781Notes

Reaction equation

HRID 1362781 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.O1CCCC1.C(=O)([O-])[O-].[Na+].[Na+].[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O>O>[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 12094240Methyl (2'-fluoro[1,1'-biphenyl]-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

47.6 g (0.21 mol) of methyl 4-bromophenylacetate are introduced under argon into 400 ml of absolute tetrahydrofuran and, at room temperature, 320 ml of 1M sodium carbonate solution and 40 g (0.28 mol) of 2-fluorophenylboronic acid are added. Addition of 7.0 g (0.01 mol) of bis(triphenylphosphane)palladium(II) chloride is followed by heating under reflux for 18 h. Cooling is followed by dilution with 500 ml of water and extracted three times with 300 ml of ethyl acetate each time. The combined organic phases are washed with 400 ml each of saturated ammonium chloride solution, water and saturated sodium chloride solution, dried over magnesium sulfate and freed of solvent in vacuo. Example V is obtained after silica gel filtration (petroleum ether/ethyl acetate 10:1) as a colorless oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 18 h
  3. temperatureCooling
  4. extractionextracted three times with 300 ml of ethyl acetate each time
  5. washThe combined organic phases are washed with 400 ml each of saturated ammonium chloride solution, water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customExample V is obtained
  8. filtrationafter silica gel filtration (petroleum ether/ethyl acetate 10:1) as a colorless oil

Sources & evidence

ORD record
ord-d0226dd4d3544808a278e6edf9d8e5c6
Source dataset
uspto-grants-2011_02
Patent number
US07883713B2

Reaction notes

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