N-bromobutanimide → 4-bromo-2-tert-butylphenylamine

HRID 1844687Notes

Reaction equation

HRID 1844687 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:19])C(=O)C1>CN(C=O)C>[Br:19][C:10]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 805742-tert-Butylaniline

Product 1

HCID 119590004-bromo-2-tert-butylphenylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-tert-butylaniline (7.5 g, 50 mmol) in DMF (80 mL) was added NBS (8.9 g, 50 mmol) at 0° C. The reaction mixture was stirred for 2 h, quenched with ice water, extracted with EA (3×100 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated and purified by CC to give compound P13a (9.1 g, 80%) as a white solid.

Workup

  1. customquenched with ice water
  2. extractionextracted with EA (3×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by CC
  8. customto give compound P13a (9.1 g, 80%) as a white solid

Sources & evidence

ORD record
ord-76d8b2b00a7f43cf9c08a1230810ce54
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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