Triphenylamine → 4-Bromotriphenylamine

HRID 1429302Notes

Reaction equation

HRID 1429302 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 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1.5 L of an ethyl acetate solution containing 54.0 g (220 mmol) of triphenylamine, 35.6 g (200 mmol) of N-Bromosuccinimide (abbreviation: NBS) was added. After that, this mixture was stirred for 24 hours. After the obtained suspension was concentrated to 1 L, the concentrated suspension was washed with 1 L of an aqueous solution containing 5% of sodium acetate. After the washing, this solution was further concentrated to about 50 mL. Then, methanol was added to the concentrated solution and the solution was precipitated. The obtained precipitate was filtered and dried to obtain 46.5 g of an objective white powder at a yield of 73%. A synthetic scheme of Step 1 is shown in (b-3) given below.

Workup

  1. additionwas added
  2. concentrationAfter the obtained suspension was concentrated to 1 L
  3. washthe concentrated suspension was washed with 1 L of an aqueous solution
  4. additioncontaining 5% of sodium acetate
  5. concentrationAfter the washing, this solution was further concentrated to about 50 mL
  6. additionThen, methanol was added to the concentrated solution
  7. customthe solution was precipitated
  8. filtrationThe obtained precipitate was filtered
  9. customdried

Sources & evidence

ORD record
ord-5055ae0d6aa04ca98c169ac03bfdd53c
Source dataset
uspto-grants-2015_01
Patent number
US08940416B2

Reaction notes

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