N-bromobutanimide → 2-Bromo-1-tert-butyl-4-nitrobenzene

HRID 2109606Notes

Reaction equation

HRID 2109606 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>C(O)(C(F)(F)F)=O.OS(O)(=O)=O>[Br:8][C:18]1[CH:17]=[C:16]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:14][C:13]=1[C:9]([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 767731-tert-Butyl-4-nitrobenzene

Product 1

HCID 2385872-Bromo-1-tert-butyl-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 86586073TFA sulfuric acidSolvent

Procedure

NBS (125.0 g, 697.5 mmol, 1.5 eq) was slowly added to a solution of TFA:H2SO4 (5:1, 750 mL) and tert-butyl-4-nitrobenzene (100.0 g, 558.0 mmol) at RT. The solution was stirred for 24 h and poured over 5 kg of ice. The resulting suspension was filtered and washed with a 1:1 MeOH:H2O solution (200 mL) and dried in a vacuum oven. MS (ES+): 258.1, 260.1 (M+H)+. Calc'd for C10H12BrNO2: 257.0.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washwashed with a 1:1 MeOH
  3. dry with materialH2O solution (200 mL) and dried in a vacuum oven

Sources & evidence

ORD record
ord-c496fb84ab024f18af85647b96a2d7a1
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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