Potassium Nitrate → 4-Bromo-2-(tert-butyl)-5-nitrophenyl methyl carbonate

HRID 423825Notes

Reaction equation

HRID 423825 reaction equation
[C:1](=[O:16])([O:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[C:12]([CH3:15])([CH3:14])[CH3:13])[O:2][CH3:3].[N+:17]([O-])([O-:19])=[O:18].[K+]>OS(O)(=O)=O>[C:1](=[O:16])([O:4][C:5]1[CH:10]=[C:9]([N+:17]([O-:19])=[O:18])[C:8]([Br:11])=[CH:7][C:6]=1[C:12]([CH3:13])([CH3:15])[CH3:14])[O:2][CH3:3]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 57470234Methyl (2-tert-butyl-4-bromophenyl) carbonate

Product 1

HCID 574702354-Bromo-2-(tert-butyl)-5-nitrophenyl methyl carbonateYield 60%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Methyl (2-tert-butyl-4-bromophenyl) carbonate (470 g, 1.67 mol) was dissolved in conc. H2SO4 (1000 ml) at 0° C. KNO3 (253 g, 2.5 mol) was added in portions over 90 min. The reaction mixture was stirred at 0° C. for 2 h and poured into ice-water (20 L). The resulting precipitate was collected via filtration and washed with water thoroughly, dried and recrystallized from ether to give methyl (2-tert-butyl-4-bromo-5-nitrophenyl) carbonate (332 g, 60% over 3 steps).

Workup

  1. filtrationThe resulting precipitate was collected via filtration
  2. washwashed with water thoroughly
  3. customdried
  4. customrecrystallized from ether

Sources & evidence

ORD record
ord-ca9527f64b6247b797a0434fb8b9545b
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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