Ethanol → 2-(3-Nitrophenyl)cyclohex-1-enecarbaldehyde

HRID 1693150Notes

Reaction equation

HRID 1693150 reaction equation
C(O)C.Br[C:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=1[CH:11]=[O:12].[N+:13]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[N+:13]([C:16]1[CH:21]=[C:20]([C:5]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:11]=[O:12])[CH:19]=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 702EthanolHCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 112639462-Bromocyclohexene-1-carbaldehyde

Product 1

HCID 578272822-(3-Nitrophenyl)cyclohex-1-enecarbaldehydeYield 73.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Ethanol (11.1 mL) was added to a solution of 2-bromocyclohex-1-enecarbaldehyde (2.22 g) in toluene (22.2 mL). 3-Nitrophenylboronic acid (2.34 g), tetrakis(triphenylphosphine)palladium (270 mg) and a 1 N sodium carbonate solution (14.0 mL) were added to the mixture. The atmosphere of the reaction system was replaced with nitrogen. Then, the reaction solution was stirred with heating under reflux for three hours. The reaction solution was cooled to room temperature, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography to obtain the title compound (2.00 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for three hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto obtain a residue
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ecc693ca22c24467becd38c37291c406
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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