Triethylamine → HCID 86620892, compound

HRID 1264355Notes

Reaction equation

HRID 1264355 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:2]=[CH2:3].Br[C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.CCN(CC)CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[C:4]1([CH2:1][CH:2]=[CH:3][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:4]1([CH:1]=[CH:2][CH2:3][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9309AllylbenzeneHCID 114644-Bromobenzoic acidHCID 11776Triphenylphosphine

Product 1

HCID 86620892HCID 86620892, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

Allylbenzene (255 μL, 1.9 mmol), 4-bromobenzoic acid (523 mg, 2.6 mmol), Et3N (0.91 mL, 6.5 mmol), Palladium (II) Acetate (16 mg, 0.052 mmol), triphenylphosphine (60 mg, 0.21 mmol) and acetonitrile (5 mL) were stirred at reflux overnight in a round bottom flask. Added HCl 1N, extracted with EtOAc, dried the organic layer on anhydrous MgSO4, filtered, evaporated solvent under vacuum. Purified by column chromatography using 10% MeOH/CH2Cl2 yielded 90 mg (14%) of mixture of two regioisomers 54. The mixture was then submitted for hydrogenation without further characterization.

Workup

  1. temperatureat reflux overnight in a round bottom flask
  2. extractionAdded HCl 1N, extracted with EtOAc
  3. dry with materialdried the organic layer on anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated solvent under vacuum
  6. customPurified by column chromatography

Sources & evidence

ORD record
ord-46e81bb2f0b34c2c905670c61bd8a56a
Source dataset
uspto-grants-2003_04
Patent number
US06541661B1

Reaction notes

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