Ethanol → HCID 20095038, compound

HRID 1770187Notes

Reaction equation

HRID 1770187 reaction equation
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](B(O)O)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[C:22]1[S:23][C:24](Br)=[CH:25][CH:26]=1.[CH2:28](O)[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:22]3[S:23][C:24]([C:14]4[CH:15]=[C:16]5[C:11](=[CH:12][CH:13]=4)[CH2:10][CH:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:28][CH3:29])[CH2:17]5)=[CH:25][CH:26]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 184532,5-DibromothiopheneHCID 220990862-Octylindane-5-boronic acid

Product 1

HCID 20095038HCID 20095038, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolvent

Procedure

0.82 g (3.0 mM) of 2-octylindan-5-boronic acid, 0.36 g (1.5 mM) of 2,5-dibromothiophene, 2 ml of ethanol, 4 ml of benzene, 4 ml of 2M-sodium carbonate aqueous solution and 0.12 g of tetrakis (triphenylphosphine)palladium (O) were mixed and heat-refluxed for 1 hour under stirring. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration under reduced pressure and purified by silica gel column chromatography (eluent: hexane/toluene=2/1) and recrystallized from a mixture solvent (toluene/methanol) to obtain 0.74 g (1.37 mM) of 2,5-bis(2-octylindan-5-yl)thiophene (Yield: 91%). ##STR326##

Workup

  1. temperatureheat-refluxed for 1 hour
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration under reduced pressure
  5. custompurified by silica gel column chromatography (eluent: hexane/toluene=2/1)
  6. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-2f8cb8448a9446ec9f61396c873681b7
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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