Water → HCID 23082997, compound

HRID 2422264Notes

Reaction equation

HRID 2422264 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1Br)[CH3:2].[CH:12]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)=[O:13].C(=O)([O-])[O-].[Na+].[Na+].O>C(OCC)(=O)C.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.C1(C)C=CC=CC=1.C(O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:12]=[O:13])[CH:19]=1)[CH3:2]

Participants

9

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 5221602-Bromo-1,3-diethylbenzeneHCID 27343563-Formylphenylboronic acid

Product 1

HCID 23082997HCID 23082997, compoundYield 81%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,3-diethyl-2-bromobenzene (3.87 g, 18.2 mmol), 3-formylphenylboronic acid (3.0 g, 20.0 mmol), tetrakistriphenylphosphinepalladium (0.84 g, 0.73 mmol), sodium carbonate (5.79 g, 54.6 mmol), water (20 mL), ethanol (20 mL) and toluene (200 mL) was heated under reflux overnight under an argon atmosphere. The reaction mixture was cooled, diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=5/1) to give the title compound (3.48 g, yield 81%) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight under an argon atmosphere
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-1f7b0d0f718e4b3bb2090e401b447b45
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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