Sodium Carbonate → HCID 22617308, compound

HRID 841847Notes

Reaction equation

HRID 841847 reaction equation
[CH2:1]([O:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22](OS(C(F)(F)F)(=O)=O)=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)[CH3:2].OB(O)[C:35]1[CH:40]=[C:39]([F:41])[C:38]([O:42][C:43]([F:46])([F:45])[F:44])=[C:37]([F:47])[CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].O>[CH2:1]([O:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:35]4[CH:40]=[C:39]([F:41])[C:38]([O:42][C:43]([F:46])([F:45])[F:44])=[C:37]([F:47])[CH:36]=4)=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 23443787B-[3,5-Difluoro-4-(trifluoromethoxy)phenyl]boronic acidHCID 54072023HCID 54072023, compound

Product 1

HCID 22617308HCID 22617308, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

6.3 g (13 mmol) of 4-(2-(4-(4-ethoxymethylcyclohexyl) cyclohexyl) ethyl) trifluoromethylsulfonyloxybenzene, 4.2 g (17 mmol) of dihydroxy (3,5-difluoro-4-trifluoromethoxyphenyl) borane, 5% palladium on activated charcoal (1.0 g) and 5.7 g (54 mmol) of sodium carbonate were refluxed in toluene/alcohol/water (1/1/1 v/v, 80 ml) under a nitrogen atmosphere for 3 days. After cooling, the reaction solution was added with water (150 ml) and extracted twice with toluene (150 ml). An organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent therein was distilled off under a reduced pressure. The residue thus obtained was purified by column chromatography (silica gel/heptane:toluene=5:1) and recrystallization (heptane-ethanol) to obtain colorless crystals of 4-(4-(2-(4-(4-ethoxymethylcyclohexyl)cyclohexyl)ethyl)phenyl)-2,6-difluorotrifluoromethoxybenzene.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with toluene (150 ml)
  3. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent therein was distilled off under a reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography (silica gel/heptane:toluene=5:1) and recrystallization (heptane-ethanol)

Sources & evidence

ORD record
ord-c1b6d4f3fe404ff78aa7c7a1464c192a
Source dataset
uspto-grants-2002_04
Patent number
US06372153B1

Reaction notes

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