Iodine → HCID 15857568, compound

HRID 1045091Notes

Reaction equation

HRID 1045091 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.II.[Mg].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1>CO.C1(C)C=CC=CC=1.CCOCC>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:21]([C:20]2[CH:19]=[CH:18][C:17]([C:16]([F:15])([F:25])[F:26])=[CH:24][CH:23]=2)=[NH:22])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 807IodineHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-2×HCID 67995Benzonitrile, 4-(trifluoromethyl)-HCID 5462224Magnesium

Product 1

HCID 15857568HCID 15857568, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

One part of 4-bromobenzotrifluoride (12.4 g, 55 mmol) and a small quantity of iodine were added to an Et2O suspension (10 mL) of magnesium (1.34 g, 55 mmol) under an argon atmosphere. And, they were heated appropriately. After the reaction start was observed, the remaining Et2O solution (15 mL) of the remaining 4-bromobenzotrifluoride was added slowly. After heat refluxing for one hour, a toluene solution (10 mL) of 4-(trifluoromethyl)benzonitrile (11.8 g, 86 mmol) was added slowly at room temperature. After heat refluxing for 20 hours, anhydrous methanol (12 mL) was added slowly at room temperature. And, the stirring-up was conducted for thirty minutes. Insoluble compounds were removed with the celite filtering. The filtrate was concentrated under reduced pressure. Thereafter, the obtained crude product was distillated under reduced pressure. And, the target product (11.9 g, 75%) was obtained. After distillation, the product was solidified.

Workup

  1. temperatureAnd, they were heated appropriately
  2. temperatureAfter heat
  3. temperaturerefluxing for one hour
  4. temperatureAfter heat
  5. temperaturerefluxing for 20 hours
  6. waitAnd, the stirring-up was conducted for thirty minutes
  7. customInsoluble compounds were removed with the celite filtering
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThereafter, the obtained crude product

Sources & evidence

ORD record
ord-e1abce5976d049a3ac7bf1c367bc3f87
Source dataset
uspto-grants-2013_10
Patent number
US08563765B2

Reaction notes

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