Ethanol → HCID 86727986, compound

HRID 2169687Notes

Reaction equation

HRID 2169687 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][CH:3]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C([O-])([O-])=O.[Na+].[Na+].CCO>C1(C)C=CC=CC=1>[Br:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:14]2[S:13][CH:17]=[CH:16][CH:15]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 665211,4-DibromonaphthaleneHCID 27339602-Thiopheneboronic acid

Product 1

HCID 86727986HCID 86727986, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 28.6 g (100 mmol) of 1,4-dibromonaphthalene, 15.35 g (120 mmol) of thiophen-2-ylboronic acid, 2.31 g (2 mmol) of tetrakis(triphenyl phosphine)palladium, 75 ml of 2M Na2CO3, 150 ml of EtOH and 300 ml toluene was degassed and placed under nitrogen, and then heated at 100° C. for 4 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica(hexane-dichloromethane) to give product (21.1 g, 73 mmol, 73%) as a white solid.

Workup

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. extractionThe organic layer was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified by column chromatography on silica(hexane-dichloromethane)

Sources & evidence

ORD record
ord-da329deafcf34c75adc1fde53d1ec683
Source dataset
uspto-grants-2015_06
Patent number
US09048437B2

Reaction notes

Loading…