Potassium Carbonate → HCID 86696077, compound

HRID 718506Notes

Reaction equation

HRID 718506 reaction equation
[CH2:1]([O:3][C:4]1[C:17]([F:18])=[C:16]2[C:7]([C:8]3[CH:9]=[CH:10][C:11]([OH:24])=[C:12]([F:23])[C:13]=3[C:14]([F:22])([F:21])[C:15]2([F:20])[F:19])=[CH:6][CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:32]1([C:41](Br)([F:43])[F:42])[CH2:37][CH2:36][CH:35]([CH2:38][CH2:39][CH3:40])[CH2:34][CH2:33]1>CN(C=O)C>[F:42][C:41]([F:43])([C:32]1[CH2:37][CH2:36][CH:35]([CH2:38][CH2:39][CH3:40])[CH2:34][CH:33]=1)[O:24][C:11]1[CH:10]=[CH:9][C:8]2[C:7]3[C:16](=[C:17]([F:18])[C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=3)[C:15]([F:19])([F:20])[C:14]([F:21])([F:22])[C:13]=2[C:12]=1[F:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86696075HCID 86696075, compoundHCID 86696078HCID 86696078, compound

Product 1

HCID 86696077HCID 86696077, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, a mixture of compound (91) (3.76 g, 10.80 mmol) and potassium carbonate (4.48 g, 32.4 mmol) was heated and agitated at 110° C. for 1 hour in a DMF (40 mL) solvent. Subsequently, 1-bromo-1-(bromodifluoromethyl)-4-propylcyclohexane (92) (7.21 g, 21.59 mmol) was added dropwise to the reaction mixture at 110° C., and the resultant mixture was further agitated for 3 hours. The reaction mixture was quenched with water, and extracted with 50 mL of toluene three times. Combined organic layers were washed with water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography, and thus 2-(difluoro(4-propylcyclohexa-1-en-1-yl)methoxy)-7-ethoxy-1,8,9,9,10,10-hexafluoro-9,10-dihydrophenanthrene (93) (4.40 g, yield 78.0%) was obtained.

Workup

  1. temperaturewas heated
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with 50 mL of toluene three times
  4. washCombined organic layers were washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationa solvent was distilled off by an evaporator
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4f0f5b0e0371443c9a2f04f4f7f435fa
Source dataset
uspto-grants-2015_11
Patent number
US09193908B2

Reaction notes

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