2-Bromoanisole → HCID 1236184, compound

HRID 430888Notes

Reaction equation

HRID 430888 reaction equation
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23].CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:2]1([C:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:14][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 113582-BromoanisoleHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxide

Product 1

HCID 1236184HCID 1236184, compoundYield 75.2%

Reagents, catalysts & solvents 3

HCID 4285986Bis[2-(diphenylphosphino)phenyl] etherCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent2×

Procedure

An oven-dried test tube was charged with tris(dibenzylideneacetone)dipalladium (4.6 mg, 0.005 mmol) and bis(2-(diphenylphosphino)phenyl)ether [DPE-phos] (8.2 mg, 0.015 mmol), capped with a rubber septum, evacuated and refilled with argon. Benzophenone imine (190 mg, 1.05 mmol), 2-bromoanisole (187 mg, 1.0 mmol) and toluene (2 mL) were added via syringe. The resulting solution was stirred at rt for 5 minutes. The tube was opened and sodium tert-butoxide (135 mg, 1.4 mmol) was added. The tube was again capped with the septum, and additional toluene (2 mL) was added via syringe to wash the solid from the test tube wall into the solution. The solution was stirred at room temperature with a gentle argon purge for 23 minutes, then heated at 80° C. for 2 hours and 10 minutes. The reaction mixture was cooled to room temperature and 1 mL ether was added. This solution was washed with saturated aqueous sodium chloride (2 mL) and the organic layer was concentrated in vacuo. The product was isolated as a yellow oil (216 mg, 75%) by flash chromatography on silica gel using 10% ethyl acetate in hexanes as eluent.

Workup

  1. customcapped with a rubber septum
  2. customevacuated
  3. additionrefilled with argon
  4. additionwas added via syringe
  5. washto wash the solid from the test tube wall into the solution
  6. stirringThe solution was stirred at room temperature with a gentle argon
  7. custompurge for 23 minutes
  8. temperatureheated at 80° C. for 2 hours and 10 minutes
  9. temperatureThe reaction mixture was cooled to room temperature
  10. addition1 mL ether was added
  11. washThis solution was washed with saturated aqueous sodium chloride (2 mL)
  12. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-20d72354aa12443c86d098ba6608033d
Source dataset
uspto-grants-2001_11
Patent number
US06323366B1

Reaction notes

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