Ethyl Acetate → 4-Bromotriphenylamine

HRID 1942979Notes

Reaction equation

HRID 1942979 reaction equation
[C:1]1([N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20]N1C(=O)CCC1=O.C(OCC)(=O)C>O>[CH:17]1[CH:16]=[CH:15][C:14]([N:7]([C:1]2[CH:2]=[CH:3][C:4]([Br:20])=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11775TriphenylamineHCID 67184N-bromobutanimide

Product 1

HCID 6428384-BromotriphenylamineYield 67.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 25 g (100 mmol) of triphenylamine, 18 g (100 mmol) of N-bromosuccinimide, and 400 mL of ethyl acetate were put in a 1000-mL Erlenmeyer flask, and the mixture was stirred at room temperature in the air for 18 hours. After the reaction was terminated, the mixture was washed with a saturated sodium carbonate aqueous solution twice to obtain an organic layer and a water layer. Then, the water layer was extracted twice with ethyl acetate, and the extract was combined with the organic layer and washed with a saturated saline solution. The solution was dried with magnesium sulfate and filtered naturally, and the filtrate was concentrated. An obtained colorless solid was recrystallized with ethyl acetate-hexane; thus, 22 g of a colorless powdered solid of 4-bromotriphenylamine was obtained (yield: 66%).

Workup

  1. customAfter the reaction was terminated
  2. washthe mixture was washed with a saturated sodium carbonate aqueous solution twice
  3. customto obtain an organic layer
  4. extractionThen, the water layer was extracted twice with ethyl acetate
  5. washwashed with a saturated saline solution
  6. dry with materialThe solution was dried with magnesium sulfate
  7. filtrationfiltered naturally
  8. concentrationthe filtrate was concentrated
  9. customAn obtained colorless solid was recrystallized with ethyl acetate-hexane

Sources & evidence

ORD record
ord-983de6e5849e49c6a9bbe6d491e4a43e
Source dataset
uspto-grants-2013_03
Patent number
US08389735B2

Reaction notes

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