1-Bromo-3-fluorobenzene → HCID 15545158, compound

HRID 430889Notes

Reaction equation

HRID 430889 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:17]=[C:18]([F:22])[CH:19]=[CH:20][CH:21]=1.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]=[C:18]([F:22])[CH:17]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 140821-Bromo-3-fluorobenzeneHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxide

Product 1

HCID 15545158HCID 15545158, compoundYield 76.3%

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), 3-bromofluorobenzene (175 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 5 minutes, then heated at 80° C. for 3 hours and 5 minutes. The reaction mixture was cooled to room temperature and washed with saturated aqueous sodium chloride (2 mL). The organic layer was filtered through celite and concentrated in vacuo. The product was isolated as a yellow solid (210 mg, 76%) by recrystalization from hot methanol.

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 5 minutes
  8. temperatureheated at 80° C. for 3 hours and 5 minutes
  9. temperatureThe reaction mixture was cooled to room temperature
  10. washwashed with saturated aqueous sodium chloride (2 mL)
  11. filtrationThe organic layer was filtered through celite and
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ccb35298d7d40fa9ba15f23b0c5a50e
Source dataset
uspto-grants-2001_11
Patent number
US06323366B1

Reaction notes

Loading…