Chlorotrimethylsilane → Methyl 2-(2-chloro-4-nitrophenyl)acetate

HRID 2077767Notes

Reaction equation

HRID 2077767 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13].[CH3:15][Si](Cl)(C)C>>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

3

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 125105882-(2-Chloro-4-nitrophenyl)acetic acid

Product 1

HCID 21876245Methyl 2-(2-chloro-4-nitrophenyl)acetateYield 74%

Procedure

To a solution of 2-(2-chloro-4-nitrophenyl)acetic acid (step 2, 4.5 g, 21 mmol) in dimethyl acetate/methanol (4/1) was added trimethylsilylchloride (0.3 ml) and stirred for 7 h at room temperature. The solvent was removed and the residue was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1) to give 3.6 g (74%) of title compound as yellow oil.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by SiO2 column chromatography with developing hexane/ethyl acetate (10/1)

Sources & evidence

ORD record
ord-47e28f710b8e4eb7b349046f6b9da5bd
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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