Water → HCID 67172297, compound

HRID 552029Notes

Reaction equation

HRID 552029 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].O.[C:18]1([CH3:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:21]2[CH2:22][CH2:23][CH:18]([CH2:24][CH2:3][CH2:2][CH2:7][CH3:6])[CH2:19][CH2:20]2)[CH:5]=[CH:6][C:7]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 1140Toluene2×HCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 67172297HCID 67172297, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
25 °C

Procedure

The compound (T-31; 20.0 g), 3-fluorophenyl boronic acid (8.20 g), potassium carbonate (22.1 g), Pd/C (NX type; 0.114 g), toluene (100 ml), Solmix A-11 (100 ml), and water (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 5 hours. The reaction mixture was cooled to 25° C., and then poured into water (300 ml) and toluene (300 ml) and mixed. Then, the mixture was allowed to stand to be separated into two layers of organic and aqueous layers, and the extraction to an organic layer was carried out. The obtained organic layer was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. The obtained solution was concentrated under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using heptane as the eluent and silica gel as the stationary phase powder. The product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11 and dried, whereby 14.2 g of 2,3′-difluoro-4-(4-pentylcyclohexyl)-1,1′-biphenyl (T-32) was obtained. The yield based on the compound (T-31) was 78%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. additionmixed
  4. customto be separated into two layers of organic and aqueous layers
  5. extractionthe extraction to an organic layer
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe obtained solution was concentrated under reduced pressure
  9. customthe residue was purified with a fractional operation by means of column chromatography
  10. customThe product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11
  11. customdried

Sources & evidence

ORD record
ord-ffb91d7f2abc4bf28b19574628554946
Source dataset
uspto-grants-2011_05
Patent number
US07951433B2

Reaction notes

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