Methyl iodide → Methyl 5-bromo-2-methyl-3-nitrobenzoate

HRID 1959279Notes

Reaction equation

HRID 1959279 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:15]([O-])([O-])=O.[Na+].[Na+].IC>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:15])=[O:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 137700085-Bromo-2-methyl-3-nitrobenzoic acid

Product 1

HCID 24727998Methyl 5-bromo-2-methyl-3-nitrobenzoateYield 109.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-2-methyl-3-nitrobenzoic acid (5.5 g, 21 mmol) in DMF (42 ml) under nitrogen, was added Na2CO3 (3.4 g, 32 mmol) followed by iodomethane (2.0 ml, 32 mmol). The reaction mixture was stirred at room temperature for 2 hours. The mixture was diluted with deionized water (150 ml) and extracted with EtOAc (4×50 ml). The combined organic phases were washed with saturated NaHCO3 (aq) (2×50 ml), dried over MgSO4, filtered and concentrated in-vacuum to give the title compound (6.3 g, 61%) as a yellow oil. LC-MS 57%, 2.20 min (3.5 minute LC-MS method), no ionization; 1H NMR (500 MHz, Chloroform-d) δ ppm 7.38 (d, J=2.05 Hz, 1H) 7.23 (d, J=2.05 Hz, 1H) 3.20 (s, 3H) 1.82 (s, 3H).

Workup

  1. extractionextracted with EtOAc (4×50 ml)
  2. washThe combined organic phases were washed with saturated NaHCO3 (aq) (2×50 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in-vacuum

Sources & evidence

ORD record
ord-87b08a6331c94735ae26fb9828bbf1af
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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