Diphenylamine → 4-Bromodiphenylamine

HRID 626604

Reaction equation

HRID 626604 reaction equation
[C:1]1([NH:7][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:14]N1C(=O)CCC1=O>C(OCC)(=O)C>[CH:11]1[CH:10]=[CH:9][C:8]([NH:7][C:1]2[CH:2]=[CH:3][C:4]([Br:14])=[CH:5][CH:6]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 11487DiphenylamineHCID 67184N-bromobutanimide

Product 1

HCID 64257864-Bromodiphenylamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 1-L conical flask, 51 g (0.3 mol) of diphenylamine was dissolved in 700 mL of ethyl acetate, and then 54 g (0.3 mol) of N-bromosuccinimide (abbreviation: NBS) was added to this solution. About 300 hours later, this mixture solution was washed with water, and then magnesium sulfate was added thereto to remove moisture. This mixture solution was filtered, and the filtrate was concentrated and collected. The object of the synthesis was obtained as 70 g of a dark brown oily substance in 94% yield.

Workup

  1. washthis mixture solution was washed with water
  2. additionmagnesium sulfate was added
  3. customto remove moisture
  4. filtrationThis mixture solution was filtered
  5. concentrationthe filtrate was concentrated
  6. customcollected
  7. customThe object of the synthesis was obtained as 70 g of a dark brown oily substance in 94% yield

Sources & evidence

ORD record
ord-24db1d85b0144160a8abbfa13e2588c5
Source dataset
uspto-grants-2016_04
Patent number
US09309223B2

Linked notes

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