Water → 3-Fluoro-4'-methoxybiphenyl

HRID 241475Notes

Reaction equation

HRID 241475 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.O>CC(C)=O>[F:8][C:4]1[CH:3]=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 140821-Bromo-3-fluorobenzeneHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 27589953-Fluoro-4'-methoxybiphenylYield 86.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

1-Bromo-3-fluorobenzene (28.8 g, 0.165 mol), potassium carbonate (50 g, 0.362 mol), 4-methoxybenzene boronic acid (27.6 g, 0.182 mol), water (100 ml) and acetone (300 ml) were placed in 1 L round-bottom three necked flask equipped with condenser, thermometer, mechanical stirrer and nitrogen inlet and outlet. The reaction flask was flushed with nitrogen and minor flow was held during whole reaction time. The mixture was heated up to the boiling point to 40° C. to degas the reaction system and then cooled down and the catalyst palladium acetate (0.1 g) was added. The temperature has increased of few degrees and the solution turned brown. The mixture was refluxed for 6 hours, then was cooled down, poured on cold water and the precipitated gray solid was filtered off. The raw product was recrystallized from ethanol (500 ml). The product (28.9 g) in a form of white crystals was obtained, 88% of theor. yield. The melting point 63-64° C.

Workup

  1. customequipped with condenser
  2. customThe reaction flask was flushed with nitrogen and minor flow
  3. customto degas the reaction system
  4. temperaturecooled down
  5. additionthe catalyst palladium acetate (0.1 g) was added
  6. temperatureThe temperature has increased of few degrees
  7. temperatureThe mixture was refluxed for 6 hours
  8. temperaturewas cooled down
  9. additionpoured on cold water
  10. filtrationthe precipitated gray solid was filtered off
  11. customThe raw product was recrystallized from ethanol (500 ml)

Sources & evidence

ORD record
ord-7b988ab2744d441d801a5f4ce285d654
Source dataset
uspto-grants-2014_02
Patent number
US08652353B2

Reaction notes

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