Water → 4-bromo-2-tert-butylphenylamine

HRID 1844689Notes

Reaction equation

HRID 1844689 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[C:9]([C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15])([CH3:12])([CH3:11])[CH3:10].O>CN(C=O)C>[Br:8][C:18]1[CH:17]=[CH:16][C:14]([NH2:15])=[C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])[CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 805742-tert-Butylaniline

Product 1

HCID 119590004-bromo-2-tert-butylphenylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of NBS (218 mg, 1 mmol) in DMF was added a solution of 2-tert-butylaniline (149 mg, 1 mmol) in DMF at rt. The reaction mixture was stirred for 4 h at rt, then water (30 mL) was added and the mixture was extracted with EA (150 mL). The organic layer was washed with brine and dried over Na2SO4, concentrated and purified by CC (hexane/EA=3/1) to give compound P19a (180 mg, 79%).

Workup

  1. extractionthe mixture was extracted with EA (150 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by CC (hexane/EA=3/1)
  6. customto give compound P19a (180 mg, 79%)

Sources & evidence

ORD record
ord-f70736e3c0114085bf1987d663d74127
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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