Potassium Carbonate → 2-(4-chlorophenyl)-5,5-dimethyl-1-Cyclohexene-1-carboxaldehyde

HRID 2406233Notes

Reaction equation

HRID 2406233 reaction equation
Br[C:2]1[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][C:3]=1[CH:10]=[O:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(Cl)Cl.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>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][C:3]=2[CH:10]=[O:11])=[CH:15][CH:14]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 251391912-Bromo-5,5-dimethylcyclohex-1-enecarbaldehyde

Product 1

HCID 445943302-(4-chlorophenyl)-5,5-dimethyl-1-Cyclohexene-1-carboxaldehydeYield 77%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 2-bromo-5,5-dimethylcyclohex-1-enecarbaldehyde (250 mg, 1.15 mmol), 4-chlorophenyl boronic acid (270 mg, 1.727 mmol) and Pd(Ph3P)4 (66.5 mg, 0.058 mmol) in dioxane (2.5 mL) was stirred at room temperature in a 5 mL microwave vial under an atmosphere of nitrogen. A solution of potassium carbonate (318 mg, 2.3 mmol) in water (0.3 mL) was added and the solution became clear. The vial was capped and heated to 100° C. for 12 minutes in a microwave. The reaction was cooled to room temperature, diluted with CH2Cl2, filtered through a plug of Celite, and concentrated. The crude residue was purified by flash chromatography on silica gel (0-25% EtOAc/heptanes) to afford 2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-enecarbaldehyde as a clear colorless oil (220 mg, 77% yield).

Workup

  1. customThe vial was capped
  2. temperatureheated to 100° C. for 12 minutes in a microwave
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationfiltered through a plug of Celite
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash chromatography on silica gel (0-25% EtOAc/heptanes)

Sources & evidence

ORD record
ord-98f82e3de3a041c3b2a671f904599cb3
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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