1,2-Dibromoethane → HCID 67979279, compound

HRID 1028354Notes

Reaction equation

HRID 1028354 reaction equation
[Mg].BrCCBr.Br[C:7]1[CH:8]=[C:9]([CH:23]=[CH:24][CH:25]=1)[N:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[B:26](OC)([O:29][CH3:30])[O:27][CH3:28]>C1COCC1>[C:11]1([N:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]2[CH:8]=[C:7]([B:26]3[O:29][CH2:30][CH2:28][O:27]3)[CH:25]=[CH:24][CH:23]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 8470Trimethyl borateHCID 5462224MagnesiumHCID 162178513-Bromo-N,N-diphenylaniline

Product 1

HCID 67979279HCID 67979279, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

First, 0.45 g of magnesium and 5 ml of THF were suspended, and a tiny amount of 1,2-dibromoethane was added to the obtained suspension. A mixed solution of 3.0 g of 3-bromo-N,N-diphenylaniline and 30 mL of THF was dripped to this suspension, and the mixture was stirred while being heated under reflux for 1.5 hours to cause a reaction. After the reaction, the solution which was naturally cooled to room temperature was cooled to −78° C., and 1.95 g of trimethyl borate was added thereto. The mixture was stirred while the temperature was increased to room temperature to cause a reaction. After the reaction, the solution was concentrated, and 4.8 mL of ethylene glycol and 30 mL of toluene were added to the obtained residue. The mixture was stirred while being heated under reflux for 12 hours to cause a reaction. After the reaction, the solution was filtered and the obtained filtrate was concentrated, so that a while solid was obtained (88% yield). The synthesis scheme of Step 1 is shown by (a-1).

Workup

  1. temperaturewhile being heated
  2. temperatureunder reflux for 1.5 hours
  3. customa reaction
  4. customAfter the reaction
  5. temperaturewas cooled to −78° C.
  6. stirringThe mixture was stirred while the temperature
  7. temperaturewas increased to room temperature
  8. customa reaction
  9. customAfter the reaction
  10. concentrationthe solution was concentrated
  11. addition4.8 mL of ethylene glycol and 30 mL of toluene were added to the obtained residue
  12. stirringThe mixture was stirred
  13. temperaturewhile being heated
  14. temperatureunder reflux for 12 hours
  15. customa reaction
  16. customAfter the reaction
  17. filtrationthe solution was filtered
  18. concentrationthe obtained filtrate was concentrated, so that a while solid
  19. customwas obtained (88% yield)
  20. customThe synthesis scheme of Step 1

Sources & evidence

ORD record
ord-9501879bb27d434cac6e65d657ec377d
Source dataset
uspto-grants-2014_05
Patent number
US08735581B2

Reaction notes

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