Sodium Carbonate → 2,3',4',5'-Tetrafluorobiphenyl-4-ol

HRID 2239198Notes

Reaction equation

HRID 2239198 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[F:10][C:11]1[CH:12]=[C:13](OB(O)O)[CH:14]=[C:15]([F:18])[C:16]=1[F:17].C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC.O>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.C1(C)C=CC=CC=1>[F:9][C:3]1[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=1[C:13]1[CH:12]=[C:11]([F:10])[C:16]([F:17])=[C:15]([F:18])[CH:14]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27791534-Bromo-3-fluorophenolHCID 18180031Water 1,2-dimethoxyethaneHCID 21870694HCID 21870694, compound

Product 1

HCID 210521442,3',4',5'-Tetrafluorobiphenyl-4-olYield 81.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Firstly, 75.0 g of 4-bromo-3-fluorophenol (S3-1), 82.9 g of 3,4,5-trifluoro-phenylboric acid (S3-2), 13.6 g of tetrakis(triphenylphosphine)palladium, 108.5 g of sodium carbonate and 1100 ml of a mixed solvent of dimethoxyethane/water=2/1 (volume ratio) were added into a reactor under nitrogen atmosphere, heated to 80° C., and stirred for 4 hours. Next, the reaction solution was cooled to room temperature, added with toluene, and then washed with 1N HCl(aq) and water. Afterwards, the solution was dried with magnesium sulphate, and distilled under reduced pressure to remove the solvent. Subsequently, the product was purified by silica-gel column chromatography with heptane/ethyl acetate (4/1) as an eluent, and then dried under reduced pressure. The obtained residue was recrystallized in heptane, to obtain 77.5 g of 3-fluoro-4-(3,4,5-trifluorophenyl)phenol (S3-3). The yield of compound (S3-3) from (S3-1) was 81.5%.

Workup

  1. temperatureNext, the reaction solution was cooled to room temperature
  2. washwashed with 1N HCl(aq) and water
  3. dry with materialAfterwards, the solution was dried with magnesium sulphate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customSubsequently, the product was purified by silica-gel column chromatography with heptane/ethyl acetate (4/1) as an eluent
  7. customdried under reduced pressure
  8. customThe obtained residue was recrystallized in heptane

Sources & evidence

ORD record
ord-fa252bcab4994fc8a691ab0ce5a151eb
Source dataset
uspto-grants-2010_05
Patent number
US07722783B2

Reaction notes

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