Dodecane → HCID 847897, compound

HRID 2253505Notes

Reaction equation

HRID 2253505 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:9][C:10]1[CH:11]=[C:12](I)[CH:13]=[C:14]([CH3:16])[CH:15]=1.[NH:18]1[CH2:22][CH2:21][CH2:20][C:19]1=[O:23].CCCCCCCCCCCC>C1(C)C=CC=CC=1>[CH3:9][C:10]1[CH:11]=[C:12]([N:18]2[CH2:22][CH2:21][CH2:20][C:19]2=[O:23])[CH:13]=[C:14]([CH3:16])[CH:15]=1

Participants

6

Reactant 4

HCID 8182DodecaneHCID 120252-PyrrolidoneHCID 62657Potassium Phosphate, TribasicHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 847897HCID 847897, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An oven-dried Schlenk flask was evacuated and backfilled with argon. The flask was charged with bis(trans-N,N′-dimethyl-1,2-cyclohexanediamine)copper(II) bromide (12.8 mg, 0.025 mmol) and K3PO4 (330 mg, 1.55 mmol) and then evacuated and backfilled with argon, and toluene (1 mL), 3,5-dimethyliodobenzene (240 mg, 1.03 mmol), 2-pyrrolidinone (108 mg, 1.26 mmol), and dodecane (160 mg, 0.94 mmol, GC internal standard) were added through a rubber septum. The septum was removed: the flask was sealed with a Teflon screwcap, and the mixture was stirred at room temperature for 2 min and then heated to 80° C. with stirring until the starting aryl iodide had been completely consumed as judged by GC analysis. The mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through Celite to give 96% GC yield of the title compound.

Workup

  1. customAn oven-dried Schlenk flask was evacuated
  2. customevacuated
  3. additionwere added through a rubber septum
  4. customThe septum was removed
  5. customthe flask was sealed with a Teflon screwcap
  6. temperatureheated to 80° C.
  7. stirringwith stirring until the starting aryl iodide
  8. customhad been completely consumed
  9. temperatureThe mixture was cooled to room temperature
  10. additiondiluted with ethyl acetate
  11. filtrationfiltered through Celite

Sources & evidence

ORD record
ord-2a9dda9eff274974bb5e39ca60d482a6
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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