Iodobenzene → HCID 66797792, compound

HRID 2275963Notes

Reaction equation

HRID 2275963 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:8][C:9]1[C:10]([NH2:22])=[CH:11][C:12]2[CH2:13][C:14]3[C:19]([C:20]=2[CH:21]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[Br:8][C:9]1[C:10]([N:22]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:11][C:12]2[CH2:13][C:14]3[C:19]([C:20]=2[CH:21]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

6

Reactant 3

HCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 2256143-Bromo-9H-fluoren-2-amine

Product 1

HCID 66797792HCID 66797792, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

8.0 g (42.2 mmol) of copper(I) iodide and 11.7 ml (97.5 mmol) of trans-cyclohexanediamine are added to a vigorously stirred suspension of 47.7 g (234 mmol) of iodobenzene, 26 g (100 mmol) of 3-bromo-9H-fluoren-2-ylamine and 416.4 g (1961 mmol) of potassium phosphate in 1170 ml of dioxane, and the mixture is heated under reflux for 16 h. After cooling, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol. Yield: 33 g (80 mmol), 80%.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol

Sources & evidence

ORD record
ord-db408bb405ac4c06a81b5f8593f1b69e
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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