Bromine → 2-Bromo-1-tert-butyl-4-nitrobenzene

HRID 74068Notes

Reaction equation

HRID 74068 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:14]Br.S([O-])(O)=O.[Na+]>S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Ag+2]>[Br:14][C:10]1[CH:9]=[C:8]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:6][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 24408BromineHCID 767731-tert-Butyl-4-nitrobenzeneHCID 23665763Sodium Bisulfite

Product 1

HCID 2385872-Bromo-1-tert-butyl-4-nitrobenzeneYield 98.4%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1-tert-butyl-4-nitrobenzene (8.95 g, 50 mmol) and silver sulfate (10 g, 32 mmol) in 50 mL of 90% sulfuric acid was added dropwise bromine (7.95 g, 50 mmol). Stirring was continued at room temperature overnight, and then the mixture was poured into dilute sodium hydrogen sulfite solution and was extracted with EtOAc three times. The combined organic layers were washed with brine and dried over MgSO4. After filtration, the filtrate was concentrated to give 2-bromo-1-tert-butyl-4-nitrobenzene (12.7 g, 98%), which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 8.47 (d, J=2.5 Hz, 1H), 8.11 (dd, J=8.8, 2.5 Hz, 1H), 7.63 (d, J=8.8 Hz, 1H), 1.57 (s, 9H); HPLC ret. time 4.05 min, 10-100% CH3CN, 5 min gradient.

Workup

  1. extractionwas extracted with EtOAc three times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2348e7a8fa9341e49a10d5fe83b6b938
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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