Methyl iodide → 1-Bromo-5-(tert-butyl)-4-methoxy-2-nitrobenzene

HRID 470045Notes

Reaction equation

HRID 470045 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([Br:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[C:16]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C.O>[C:1]([C:5]1[CH:10]=[C:9]([Br:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[O:15][CH3:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 574702362-Tert-butyl-4-bromo-5-nitrophenol

Product 1

HCID 574702451-Bromo-5-(tert-butyl)-4-methoxy-2-nitrobenzeneYield 69.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-tert-butyl-4-bromo-5-nitrophenol (C-14-a) (1.5 g, 5.5 mmol) and Cs2CO3 (2.2 g, 6.6 mmol) in DMF (6 mL) was added methyl iodide (5150 μL, 8.3 mmol). The mixture was stirred at room temperature for 4 h, diluted with H2O and extracted twice with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. After removal of solvent, the residue was washed with hexane to yield 1-tert-butyl-2-methoxy-5-bromo-4-nitrobenzene (1.1 g, 69%). 1H NMR (400 MHz, CDCl3) δ 7.58 (s, 1H), 7.44 (s, 1H), 3.92 (s, 3H), 1.39 (s, 9H).

Workup

  1. extractionextracted twice with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customAfter removal of solvent
  5. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-cf60ac4f10c14fc8b1167a86e506a299
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

Loading…