Triphenylamine → 4-Bromotriphenylamine

HRID 1408277Notes

Reaction equation

HRID 1408277 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>[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

4

Reactant 2

HCID 11775TriphenylamineHCID 67184N-bromobutanimide

Product 1

HCID 6428384-BromotriphenylamineYield 67.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

25 g (100 mmol) of triphenylamine, 18 g (100 mmol) of N-bromosuccinimide, and 400 mL of ethyl acetate were put into a 1000 mL Erlenmeyer flask, and were stirred for approximately 12 hours at the room temperature in the air to be reacted. After the reaction was completed, the reaction solution was washed twice with a saturated sodium carbonate solution to separate an aqueous layer and an organic layer. Then, the aqueous 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 then filtration was performed. The filtrate was concentrated, and an obtained solid of 4-bromotriphenylamine was re-crystallized with ethyl acetate and hexane, whereby 22 g of a white powder solid was obtained in the yield of 66% (Synthesis Scheme (i-1)).

Workup

  1. customto be reacted
  2. washthe reaction solution was washed twice with a saturated sodium carbonate solution
  3. customto separate an aqueous layer
  4. extractionThen, the aqueous 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. filtrationfiltration
  8. concentrationThe filtrate was concentrated
  9. customan obtained solid of 4-bromotriphenylamine was re-crystallized with ethyl acetate and hexane

Sources & evidence

ORD record
ord-37e274c555c642de94ddec585a88207f
Source dataset
uspto-grants-2014_12
Patent number
US08920941B2

Reaction notes

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