Diphenylamine → 4-Bromodiphenylamine

HRID 1805967

Reaction equation

HRID 1805967 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, the filtrate was concentrated, and the resulting substance was collected. Accordingly, a dark brown oily substance, which was the substance to be produced, was obtained, and the amount and yield of the substance were 70 g and 94%, respectively.

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. customthe resulting substance was collected
  7. customto be produced
  8. customwas obtained

Sources & evidence

ORD record
ord-230efc1e2f254f588457384f9fd7689a
Source dataset
uspto-grants-2013_01
Patent number
US08354542B2

Linked notes

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