Potassium Carbonate → HCID 178444266, compound

HRID 2260904Notes

Reaction equation

HRID 2260904 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[F:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O>[F:19][C:20]1[CH:21]=[C:22]([C:2]2[CH:3]=[CH:4][C:5]([C@H:8]3[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]3)=[CH:6][CH:7]=2)[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 178444344HCID 178444344, compound

Product 1

HCID 178444266HCID 178444266, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

Into a reaction vessel under an atmosphere of nitrogen, 1-iodo-4-(trans-4-pentylcyclohexyl)benzene (T26; 50.0 g), 3-fluorophenylboronic acid (T27; 21.5 g), potassium carbonate (58.0 g), Pd (Ph3P)2Cl2 (2.95 g), water (200 ml), toluene (200 ml), and Solmix A-11 (200 ml) were put and heated under reflux for 8 hours. After the reaction mixture had been cooled to 25° C., the solution was poured into water (1,000 ml) and toluene (500 ml) and mixed. The mixture was then allowed to stand to be separated into two layers of an organic layer and an aqueous layer. Extraction into an organic layer was carried out and the resulting organic layer was fractionated. The extracts were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by means of fraction-collecting column chromatography using heptane as the eluent and silica gel as the stationary phase powder. The residue was further purified by recrystallization from a mixed solvent of ethyl acetate and Solmix A-11 (volume ratio of ethyl acetate Solmix A-11=1:1) and then dried, whereby 37.3 g of 3-fluoro-4′-(trans-4-pentylcyclohexyl)biphenyl (T28) was obtained. The yield based on the compound (T26) was 82.0%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 8 hours
  3. additionmixed
  4. customto be separated into two layers of an organic layer
  5. extractionExtraction into an organic layer
  6. washThe extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe resulting solution was concentrated under reduced pressure
  9. customthe residue was purified by means
  10. customof fraction-collecting column chromatography
  11. customThe residue was further purified by recrystallization from a mixed solvent of ethyl acetate and Solmix A-11 (volume ratio of ethyl acetate Solmix A-11=1:1)
  12. customdried

Sources & evidence

ORD record
ord-f0bd51b34e2c48f9a0cf05e4af89f69b
Source dataset
uspto-grants-2010_12
Patent number
US07846514B2

Reaction notes

Loading…