Dimethylformamide → Methyl 3-iodo-5-nitrobenzoate

HRID 1070403Notes

Reaction equation

HRID 1070403 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].[C:14](Cl)(=O)C(Cl)=O.CN(C=O)C.C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C.O.CO>[CH3:14][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

9

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 805803-Iodo-5-nitrobenzoic acid

Product 1

HCID 7020599Methyl 3-iodo-5-nitrobenzoateYield 98%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-iodo-5-nitro-benzoic acid (5.88 g, 20.07 mmol) in dichloromethane (60 mL) at room temperature under nitrogen was added oxalyl chloride (1.92 mL, 24.28 mmol) and a drop of DMF. The mixture was stirred for 1 h. methanol (20 mL), DMAP (0.245 g, 2.00 mmol), and triethylamine (3.08 mL, 24.28 mmol) were added and the mixture was stirred for an additional 2 h. Water was added and the product was extracted, washed with water, then brine, dried over magnesium sulfate and concentrated to dryness. Purification by chromatography gave 6.04 g of 3-iodo-5-nitro-benzoic acid methyl ester, as a yellow solid.

Workup

  1. additionwere added
  2. extractionthe product was extracted
  3. washwashed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-d4b4485a4b6a48a1a0d1816fa626fb03
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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