Water → Methyl 4-bromo-2-nitrobenzoate

HRID 906598Notes

Reaction equation

HRID 906598 reaction equation
[Br: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.CI.O>CN(C=O)C>[CH3:14][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 37744674-Bromo-2-nitrobenzoic acid

Product 1

HCID 18350461Methyl 4-bromo-2-nitrobenzoateYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-nitrobenzoic acid (25.3 g, 103 mmol) in DMF (200 mL) at 0° C. were added DBU (79.1 mL, 514.8 mmol) and MeI (32.2 mL, 515 mmol). The reaction mixture was stirred for 15 min at this temperature and for 72 h at r.t. The mixture was poured into water and extracted with EtOAc (2×). The combined organic layers were washed with water (2×), dried (Na2SO4) and the solvent was removed in vacuo. The residue was purified by flash chromatography (silica gel, 7:3 hexanes:EtOAc) to provide the title compound (26.24 g, 98%) as a yellow oil.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with water (2×)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by flash chromatography (silica gel, 7:3 hexanes:EtOAc)

Sources & evidence

ORD record
ord-ca4b4bf2160948b3bf006677e4d0ba1b
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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