Triethylamine → HCID 86620892, compound

HRID 2402419Notes

Reaction equation

HRID 2402419 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 μμL, 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-2fed519734d44cea86f2a8db757bf2b3
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

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