HCID 17841554, compound → HCID 58471577, compound

HRID 1038272Notes

Reaction equation

HRID 1038272 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:15]1[CH:20]=[C:19]([F:21])[C:18]([C:22]([F:44])([F:43])[O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[C:34]([F:36])[C:33]([C:37]([F:40])([F:39])[F:38])=[C:32]([F:41])[CH:31]=3)=[C:26]([F:42])[CH:25]=2)=[C:17]([F:45])[CH:16]=1.[OH-].[NH3+]N>C1COCC1.O.CC(OC)(C)C.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>[F:43][C:22]([F:44])([C:18]1[C:19]([F:21])=[CH:20][C:15]([C:3]2[CH:4]=[CH:5][C:6]([CH2:8][CH2:9][CH3:10])=[CH:7][C:2]=2[F:1])=[CH:16][C:17]=1[F:45])[O:23][C:24]1[CH:25]=[C:26]([F:42])[C:27]([C:30]2[CH:35]=[C:34]([F:36])[C:33]([C:37]([F:40])([F:39])[F:38])=[C:32]([F:41])[CH:31]=2)=[CH:28][CH:29]=1

Participants

7

Reactant 3

HCID 17841554HCID 17841554, compoundHCID 44558531Aminoammonium hydroxideHCID 58471583HCID 58471583, compound

Product 1

HCID 58471577HCID 58471577, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 15413tert-Butyl methyl etherSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 2.60 g (14.3 mmol) of 2-fluoro-4-propylbenzeneboronic acid, 7.0 g (13.1 mmol) of 4′-[(4-bromo-2,6-difluorophenyl)difluoromethoxy]-3,5,2′-trifluoro-4-trifluoromethylbiphenyl, 0.30 g (0.42 mmol) of bis(triphenyl-phosphine)palladium(II) chloride and 2.80 g (10.1 mmol) of sodium metaborate octahydrate is initially introduced in 40 ml of THF/water=3:1. 0.02 ml (0.4 mmol) of hydrazinium hydroxide is added, and the mixture is refluxed for 20 h. After cooling, the batch is diluted with MTBE, and the mixture is washed with water. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with water. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 4-[difluoro(3,5,2′-trifluoro-4′-propyl-biphenyl-4-yl)methoxy]-6,3′,5′-trifluoro-4′-trifluoromethylbiphenyl as a colourless solid.

Workup

  1. temperaturethe mixture is refluxed for 20 h
  2. temperatureAfter cooling
  3. washthe mixture is washed with water
  4. customThe organic phase is separated off
  5. extractionthe aqueous phase is extracted with MTBE
  6. washThe combined organic phases are washed with water
  7. customThe solution is dried
  8. concentrationconcentrated to dryness
  9. customThe residue is purified by column chromatography (SiO2, n-heptane)
  10. customThe further purification
  11. customis carried out by recrystallisation from ethanol and n-heptane

Sources & evidence

ORD record
ord-4ebd314b48644dc9bd24bbde8624e18b
Source dataset
uspto-grants-2013_10
Patent number
US08551359B2

Reaction notes

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