Aminoammonium hydroxide → HCID 58471579, compound

HRID 1038273Notes

Reaction equation

HRID 1038273 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9](Br)=[C:8]([F:13])[CH:7]=1)[CH2:2][CH2:3][CH3:4].FC(F)(O[C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[C:44]([F:46])[C:43]([C:47]([F:50])([F:49])[F:48])=[C:42]([F:51])[CH:41]=2)=[C:36]([F:52])[CH:35]=1)C1C(F)=CC(B2OC(C)(C)C(C)(C)O2)=CC=1F.[OH-:54].[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:49][C:47]([F:48])([C:43]1[C:42]([F:51])=[CH:41][C:40]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][C:8]=2[F:13])=[CH:45][C:44]=1[F:46])[O:54][C:34]1[CH:35]=[C:36]([F:52])[C:37]([C:40]2[CH:41]=[C:42]([F:51])[C:43]([C:47]([F:50])([F:49])[F:48])=[C:44]([F:46])[CH:45]=2)=[CH:38][CH:39]=1

Participants

7

Reactant 3

HCID 44558531Aminoammonium hydroxideHCID 58471580HCID 58471580, compoundHCID 58471582HCID 58471582, compound

Product 1

HCID 58471579HCID 58471579, compound

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 4.55 g (18.4 mmol) of 4-butoxy-2-fluorobromobenzene, 9.10 g (15.7 mmol) of 2-{4-[difluoro-(2,3′,5′-trifluoro-4′-trifluoromethylbiphenyl-4-yloxy)methyl]-3,5-difluorophenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.36 g (0.50 mmol) of bis(triphenylphosphine)palladium(II) chloride and 3.35 g (12.0 mmol) of sodium metaborate octahydrate is initially introduced in 60 ml of THF/water=4:1. 0.024 ml (0.5 mmol) of hydrazinium hydroxide is added, and the mixture is refluxed for 19 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:toluene=9:1→3:1). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 4-[difluoro(3,5,2′-trifluoro-4′-butoxybiphenyl-4-yl)methoxy]-6,3′,5′-trifluoro-4′-trifluoromethylbiphenyl as a colourless solid.

Workup

  1. temperaturethe mixture is refluxed for 19 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:toluene=9:1→3:1)
  10. customThe further purification
  11. customis carried out by recrystallisation from ethanol and n-heptane

Sources & evidence

ORD record
ord-c2ca34fd6b504c938d52a90d85b7c9cf
Source dataset
uspto-grants-2013_10
Patent number
US08551359B2

Reaction notes

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