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

HRID 655935Notes

Reaction equation

HRID 655935 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:15](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:15])=[O:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 534307765-Fluoro-3-methyl-2-nitrobenzoic acid

Product 1

HCID 53415166Methyl 5-fluoro-3-methyl-2-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (E1) and cesium carbonate (1.5 eq.) in DMF (0.25 M) at RT was added methyl iodide (1.0 eq.). After the mixture was stirred for 18 h, brine was added and the mixture was extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The yellow solid was used in the next step without purification. 1H NMR (400 MHz, DMSO, 300K) δ 7.63 (2H, m), 3.83 (3H, s), 2.29 (3H, s).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe yellow solid was used in the next step without purification

Sources & evidence

ORD record
ord-eb1d0b75953d4e298139b60ae155ebf8
Source dataset
uspto-grants-2011_12
Patent number
US08071623B2

Reaction notes

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