Toluene → 4-(4-(Hexyloxy)phenyl)thiophene-2-carbaldehyde

HRID 1892086Notes

Reaction equation

HRID 1892086 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Br[C:18]1[CH:19]=[C:20]([CH:23]=[O:24])[S:21][CH:22]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:18]2[CH:19]=[C:20]([CH:23]=[O:24])[S:21][CH:22]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 877924-Bromothiophene-2-carbaldehydeHCID 36821484-Hexyloxyphenylboronic Acid

Product 1

HCID 594097744-(4-(Hexyloxy)phenyl)thiophene-2-carbaldehydeYield 52.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of commercial available 4-(hexyloxy)phenylboronic acid (25, 5.55 g, 25.0 mmol), 4-bromothiophene-2-carbaldehyde (5.25 g, 27.5 mmol), tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.13 mmol), toluene (25 mL), ethanol (15 mL) and aqueous sodium carbonate (2 M, 25 mL) was stirred under reflux for 18 hours under a nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and the aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with saturated sodium chloride (50 mL), and dried over magnesium sulfate. After filtration and concentration, the crude material was purified by recrystallization from ethyl acetate/petroleum ether (1/2, v/v) to afford the compound 1026 (3.8 g).

Workup

  1. temperatureunder reflux for 18 hours under a nitrogen atmosphere
  2. extractionthe aqueous layer was extracted with dichloromethane (3×50 mL)
  3. washThe combined organic layers were washed with saturated sodium chloride (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe crude material was purified by recrystallization from ethyl acetate/petroleum ether (1/2

Sources & evidence

ORD record
ord-3f516509f5d240c78d6691f8936925ce
Source dataset
uspto-grants-2013_08
Patent number
US08507647B2

Reaction notes

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