Water → 4-Bromo-2,6-diisopropylaniline

HRID 539445Notes

Reaction equation

HRID 539445 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH:9]([C:12]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[C:13]=1[NH2:14])([CH3:11])[CH3:10].O>CN(C=O)C>[Br:8][C:17]1[CH:18]=[C:12]([CH:9]([CH3:11])[CH3:10])[C:13]([NH2:14])=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 32484DiisopropylanilineHCID 67184N-bromobutanimide

Product 1

HCID 117801144-Bromo-2,6-diisopropylanilineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A solution of NBS (24.59 g, 137 mmol) in DMF (160 mL) was added slowly to a solution of 2,6-diisopropylaniline (25 g, 137 mmol) in DMF (300 mL) at 0-5° C. under a nitrogen atmosphere over a period of 20 minutes. The reaction mixture was stirred at 0-5° C. After the reaction was complete, water was added and the oil suspension was stirred at rt. The aqueous layer was decanted out and the remaining oil was dissolved in ethyl acetate. The organic layer was separated, washed water and brine. Evaporation gave light brown oil (35.1 g, 100% yield).

Workup

  1. stirringthe oil suspension was stirred at rt
  2. customThe aqueous layer was decanted out
  3. dissolutionthe remaining oil was dissolved in ethyl acetate
  4. customThe organic layer was separated
  5. washwashed water and brine
  6. customEvaporation

Sources & evidence

ORD record
ord-30f6853a89ff443cb07b4f18d940dd44
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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