Water → 4-Bromo-2,6-diisopropylaniline

HRID 64539Notes

Reaction equation

HRID 64539 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].[Br:14]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:14][C:9]1[CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]([NH2:6])=[C:7]([CH:11]([CH3:13])[CH3:12])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 32484DiisopropylanilineHCID 67184N-bromobutanimide

Product 1

HCID 117801144-Bromo-2,6-diisopropylanilineYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A three neck round bottom flask was charged with 2,6-diisopropylaniline (22.96 g, 130 mmol) and DMF (Volume: 250 ml). A solution of 1-bromopyrrolidine-2,5-dione (23.05 g, 130 mmol) in 100 ml DMF was added into reaction mixture drop wise at 0° C. After addition was over; reaction mixture was stirred for 2 days at room temperature. The reaction mixture was poured into 500 ml deionized water and extracted with 3×150 ml ether. The combined extracts were washed with 150 ml deionized water, 150 ml 10% lithium chloride, dried over MgSO4 and evaporated to dryness. The residue was purified by vacuum distillation to yield 4-bromo-2,6-diisopropylaniline (32.3 g; 97%).

Workup

  1. additionAfter addition
  2. customreaction mixture
  3. additionThe reaction mixture was poured into 500 ml
  4. extractionextracted with 3×150 ml ether
  5. washThe combined extracts were washed with 150 ml
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. distillationThe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-f1ca211cff014226af9eeb4cc8c7f514
Source dataset
uspto-grants-2016_09
Patent number
US09450195B2

Reaction notes

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