1,3-Propanediol → HCID 58729335, compound

HRID 552875Notes

Reaction equation

HRID 552875 reaction equation
[C:1]1(B(O)O)[C:9]([CH3:10])=[C:7]([CH3:8])[CH:6]=[C:4]([CH3:5])[C:2]=1[CH3:3].[CH2:14](O)[CH2:15][CH2:16]O.Br[C:20]1[CH:32]=[CH:31][C:30]2[C:29]3[C:24](=[CH:25][C:26](Br)=[CH:27][CH:28]=3)[C:23]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:22]=2[CH:21]=1.C([O-])([O-])=O.[K+].[K+]>O.C1(C)C=CC=CC=1>[CH3:3][C:2]1[C:4]([CH3:5])=[CH:6][C:7]([CH3:8])=[C:9]([CH3:10])[C:1]=1[C:20]1[CH:32]=[CH:31][C:30]2[C:29]3[C:24](=[CH:25][C:26]([C:14]4[C:4]([CH3:5])=[C:2]([CH3:3])[CH:1]=[C:9]([CH3:7])[C:15]=4[CH3:16])=[CH:27][CH:28]=3)[C:23]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:22]=2[CH:21]=1

Participants

7

Reactant 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 16213799(2,3,5,6-Tetramethylphenyl)boronic acidHCID 534239202,7-Dibromo-9,9-diheptyl-9H-fluorene

Product 1

HCID 58729335HCID 58729335, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

0.04 mol of durylboronic acid is initially charged in a 1-liter 3-neck flask with 600 ml of toluene, admixed with 0.04 mol of propane-1,3-diol and heated on a water separator until no further water is separated out. Afterward, the water separator is removed and replaced by a reflux condenser, and 0.01 mol of 2,7-dibromo-9,9-diheptylfluorene and 11.6 g of potash dissolved in 42 ml of water are added to the reaction mixture. The flask is then repeatedly evacuated under reduced pressure and flooded with argon in order to add the catalyst, tetrakis(triphenylphosphine)palladium. Finally, the mixture is heated to 110° C. for 48 h and purged with argon during this time. For workup, the organic phase is washed repeatedly with water, extracted and concentrated to dryness. The residue is washed in methanol and filtered off with suction. The crude product is purified by chromatography on silica gel by means of cyclohexane.

Workup

  1. customis separated out
  2. customAfterward, the water separator is removed
  3. customreplaced by a reflux condenser
  4. additionare added to the reaction mixture
  5. customThe flask is then repeatedly evacuated under reduced pressure
  6. additionto add the catalyst, tetrakis(triphenylphosphine)palladium
  7. custompurged with argon during this time
  8. washFor workup, the organic phase is washed repeatedly with water
  9. extractionextracted
  10. concentrationconcentrated to dryness
  11. washThe residue is washed in methanol
  12. filtrationfiltered off with suction
  13. customThe crude product is purified by chromatography on silica gel by means of cyclohexane

Sources & evidence

ORD record
ord-2418f3247d5d47709a2ef66e614d261e
Source dataset
uspto-grants-2011_05
Patent number
US07951874B2

Reaction notes

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