Sodium Carbonate → HCID 58444573, compound

HRID 1509764Notes

Reaction equation

HRID 1509764 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][CH3:21])[CH2:15][O:14]2)=[CH:9][C:8]=1[F:22])(=O)=O.[F:25][C:26]1[CH:27]=[C:28]([CH:50]=[C:51]([F:57])[C:52]=1[C:53]([F:56])([F:55])[F:54])[O:29][C:30]([F:49])([F:48])[C:31]1[C:36]([F:37])=[CH:35][C:34](B2OC(C)(C)C(C)(C)O2)=[CH:33][C:32]=1[F:47].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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>[F:25][C:26]1[CH:27]=[C:28]([CH:50]=[C:51]([F:57])[C:52]=1[C:53]([F:54])([F:56])[F:55])[O:29][C:30]([F:48])([F:49])[C:31]1[C:32]([F:47])=[CH:33][C:34]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][O:14]3)=[CH:9][C:8]=2[F:22])=[CH:35][C:36]=1[F:37]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 58444581HCID 58444581, compoundHCID 86657880HCID 86657880, compound

Product 1

HCID 58444573HCID 58444573, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 10.0 g (27.0 mmol) of 2-fluoro-4-(trans-5-propyltetrahydropyran-2-yl)phenyl trifluoromethanesulfonate and 14.3 g (29.4 mmol) of 2-{4-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-3,5-difluorophenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolan, 1.50 g (1.30 mmol) of tetrakis(triphenylphosphine)palladium(0) and 30 ml of 2 N sodium carbonate solution in 100 ml of toluene/ethanol (1:1) is heated under reflux for 20 h. After cooling, 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=7:3). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 2-{4′-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-2,3′,5′-trifluorobiphenyl-4-yl}-5-propyltetrahydropyran as a colourless solid (m.p. 95° C.).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 20 h
  3. temperatureAfter cooling
  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=7:3)
  10. customThe further purification
  11. customis carried out by recrystallisation from ethanol and n-heptane

Sources & evidence

ORD record
ord-ce845fbdcc324a7091d9509728baa28a
Source dataset
uspto-grants-2012_07
Patent number
US08211513B2

Reaction notes

Loading…