Sulfuric Acid → 2-Bromo-1-tert-butyl-4-nitrobenzene

HRID 2109632Notes

Reaction equation

HRID 2109632 reaction equation
[Br:1]Br.[C:3]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].OS(O)(=O)=O>S([O-])([O-])(=O)=O.[Ag+2].O>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[Br:1])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 24408BromineHCID 767731-tert-Butyl-4-nitrobenzene

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 962WaterSolvent

Procedure

Bromine (17.4 ml) was added dropwise over 40 min to a stirred mixture of 4-tert-butylnitrobenzene (59.5 g, 332 mmol), silver(II)sulfate (56.5 g, 181 mmol), H2SO4 (300 ml), and H2O (33 ml) at RT. The mixture was stirred for a further 3 h and then poured into 0.1 M Na2S2O5/H2O (1 L). The solid was filtered, washed with H2O, Et2O, and CH2Cl2. The filtrate layers were separated. The aqueous fraction was extracted with Et2O. The combined organic layers were combined, dried over Na2SO4, and concentrated in vacuo. The yellow solid was triturated with hexanes to give a pale yellow crystalline solid.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with H2O, Et2O, and CH2Cl2
  3. customThe filtrate layers were separated
  4. extractionThe aqueous fraction was extracted with Et2O
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe yellow solid was triturated with hexanes
  8. customto give a pale yellow crystalline solid

Sources & evidence

ORD record
ord-746ef378d5194a38a336c8841d57b9f4
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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