Water → Methyl 4-iodo-2-nitrobenzoate

HRID 1672173Notes

Reaction equation

HRID 1672173 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[CH2:14]1CCN2C(=NCCC2)CC1.IC.O>CN(C=O)C>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:14])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 189198834-Iodo-2-nitrobenzoic acid

Product 1

HCID 58476577Methyl 4-iodo-2-nitrobenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-iodo-2-nitrobenzoic acid (2.3 g, 7.9 mmol) in DMF (30 mL) was added DBU (2.4 mL, 16 mmol) followed by iodomethane (1.5 mL, 24 mmol). The reaction mixture was allowed to stir at 0° C. for 15 min, then slowly allowed to warm to rt and to stir overnight. After 12 h, the reaction mixture was poured into 200 mL of H2O and extracted with EtOAc (2×100 mL). The organic solutions were combined, washed with H2O (2×100 mL), dried over Na2SO4, filtered and concentrated to give methyl 4-iodo-2-nitrobenzoate (2.3 g, 96%).

Workup

  1. temperatureto warm to rt
  2. stirringto stir overnight
  3. waitAfter 12 h
  4. extractionextracted with EtOAc (2×100 mL)
  5. washwashed with H2O (2×100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c4832796fd754b3db11b7bb2d7599b02
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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