Potassium Carbonate → HCID 19108125, compound

HRID 1943545Notes

Reaction equation

HRID 1943545 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:13][C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.O>[CH2:5]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([F:13])[C:19]=2[F:20])=[CH:9][CH:8]=1)[CH2:4][CH2:3][CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 70986(4-Bromobutoxy)benzeneHCID 2734333(2,3-Difluorophenyl)boronic acid

Product 1

HCID 19108125HCID 19108125, compoundYield 78.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

4-Bromobutoxybenzene (16) (50.0 g), 2,3-difluorophenylboronic acid (17) (37.9 g), potassium carbonate (90.5 g), Pd(Ph3P)2Cl2 (4.6 g), toluene (200 ml), Solmix A-11 (200 ml) and water (200 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 2 hours. The reaction mixture was cooled to 25° C., and then poured into water (500 ml) and toluene (500 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure, and the residue obtained was purified with a fractional operation by means of column chromatography using toluene as the eluent and silica gel as the stationary phase powder. The product was further purified by means of recrystallization from Solmix A-11 and dried, giving 44.7 g of 4′-butoxy-2,3-difluoro-1,1′-biphenyl (18). The yield based on the compound (16) was 78.1%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. additionmixed
  4. customhad separated into two phases of organic and
  5. extractionaqueous phases, and extraction into an organic phase
  6. customThe organic phase obtained
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solution obtained
  10. concentrationwas concentrated under reduced pressure
  11. customthe residue obtained
  12. customwas purified with a fractional operation by means of column chromatography
  13. customThe product was further purified by means of recrystallization from Solmix A-11
  14. customdried

Sources & evidence

ORD record
ord-37d3218d891c4806bd69160ebf374d84
Source dataset
uspto-grants-2013_03
Patent number
US08394294B2

Reaction notes

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