Methanol → Methyl 3-iodo-5-nitrobenzoate

HRID 340615

Reaction equation

HRID 340615 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:18]O>>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=[C:2]([I:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 805803-Iodo-5-nitrobenzoic acid

Product 1

HCID 7020599Methyl 3-iodo-5-nitrobenzoateYield 99%

Procedure

To a solution of 3-iodo-5-nitrobenzoic acid (20.00 g, 0.068 mol) in methanol (50 mL) was added SOCl2 (5.45 mL, 0.075 mol) at 0° C. The reaction mixture was allowed to warm to room temperature and was then heated to breflux for 2 hours. The reaction was cooled and solvent was removed in vacuo to afford 3-Iodo-5-nitro-benzoic acid methyl ester as light yellow solid (20.67 g, 99%). MS (M+H)=309.

Workup

  1. temperaturewas then heated
  2. temperatureThe reaction was cooled
  3. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-f432f7a953304c8eb4589c665dcee18c
Source dataset
uspto-grants-2014_11
Patent number
US08895589B2

Linked notes

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