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

HRID 2213526Notes

Reaction equation

HRID 2213526 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.C(=O)([O-])[O-].[Na+].[Na+].[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O>O1CCCC1.O>[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=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 3

HCID 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 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 47.6 g (0.21 mol) of methyl 4-bromophenylacetate are initially charged in 400 ml of absolute tetrahydrofuran and, at room temperature, admixed with 320 ml of 1M sodium carbonate solution and 40 g of (0.28 mol) of 2-fluorophenylboronic acid. 7.0 g (0.01 mol) of bis(triphenylphosphane)palladium(II) chloride are added, and the mixture is then heated under reflux for 18 h. After cooling, the mixture is diluted with 500 ml of water and extracted three times with in each case 300 ml of ethyl acetate. The combined organic phases are washed with in each case 400 ml of saturated ammonium chloride solution, water and saturated sodium chloride solution, dried over magnesium sulphate and freed from the solvent under reduced pressure. Example V is obtained after silica gel filtration (petroleum ether/ethyl acetate 10:1) as a colourless oil.

Workup

  1. temperaturethe mixture is then heated
  2. temperatureunder reflux for 18 h
  3. temperatureAfter cooling
  4. extractionextracted three times with in each case 300 ml of ethyl acetate
  5. washThe combined organic phases are washed with in each case 400 ml of saturated ammonium chloride solution, water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. customExample V is obtained
  8. filtrationafter silica gel filtration (petroleum ether/ethyl acetate 10:1) as a colourless oil

Sources & evidence

ORD record
ord-41dac96c092348c1bbe85a667e44ac4e
Source dataset
uspto-grants-2006_09
Patent number
US07105553B2

Reaction notes

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