Trimethyl orthoacetate → Methyl 4-iodo-3-nitrobenzoate

HRID 2044211Notes

Reaction equation

HRID 2044211 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14](OC)(OC)(OC)C>>[CH3:14][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

3

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 112085984-Iodo-3-nitrobenzoic acid

Product 1

HCID 297884Methyl 4-iodo-3-nitrobenzoateYield 99%

Procedure

A solution of 4-iodo-3-nitrobenzoic acid (3 g, 10 mmol) in trimethyl orthoacetate (30 ml) is refluxed (˜110° C.) for 15 hours and then solvent is evaporated under reduced pressure. The 4-iodo-3-nitrobenzoic acid methyl ester is obtained as a yellow solid (3.11 g, 99% yield, 97.5% HPLC).

Workup

  1. customsolvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-473861520cee4a66bf941ec762f4d455
Source dataset
uspto-grants-2013_11
Patent number
US08586792B2

Reaction notes

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