Water → 4-Bromo-2,6-diisopropylaniline

HRID 526760Notes

Reaction equation

HRID 526760 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].C1C(=O)N([Br:21])C(=O)C1.O>CN(C)C=O>[Br:21][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 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2,6-diisopropylaniline (14 g, 78.97 mmol, 1.00 equiv) in N,N-dimethylformamide (200 mL) at 0° C. was added a solution of NBS (14 g, 78.65 mmol, 1.00 equiv) in N,N-dimethylformamide (100 mL) dropwise in 60 min. The reaction was stirred for another hour at 0° C. then water (900 mL) was added. The resulting mixture was extracted with 300 mL of ethyl acetate. The combined organic layers was washed with 3×100 mL of saturated NH4Cl solution and 1×100 mL of water then dried over anhydrous sodium sulfate and concentrated under vacuum to give 20.05 g (99%) of 4-bromo-2,6-diisopropylaniline as a red oil. 1H NMR (400 MHz, DMSO-d6): δ 6.95 (s, 2H), 4.77 (s, 2H), 5.47-5.39 (m, 1H), 3.04-2.98 (m, 1H), 1.13 (d, J=6.8 Hz, 12H) ppm.

Workup

  1. extractionThe resulting mixture was extracted with 300 mL of ethyl acetate
  2. washThe combined organic layers was washed with 3×100 mL of saturated NH4Cl solution and 1×100 mL of water
  3. dry with materialthen dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8f342c4bc5c14013b9cb49280221fb0e
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Reaction notes

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