Dimethylformamide → 2-Chloro-5-iodobenzoyl chloride

HRID 628752Notes

Reaction equation

HRID 628752 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C)C=O.C(Cl)(=O)C([Cl:20])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([Cl:20])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 5196382-Chloro-5-iodobenzoic acid

Product 1

HCID 47693022-Chloro-5-iodobenzoyl chlorideYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-chloro-5-iodobenzoic acid (10.0 g, 35.5 mmol) was suspended in methylene chloride (200 mL). To the resulting mixture was added N,N-dimethylformamide (0.05 mL), and then added dropwise oxalyl chloride (11.3 g, 89.0 mmol) at 0° C. After the completion of dropwise addition, the resulting mixture was warmed up to room temperature and stirred for 4 hr. The resulting clear solution was evaporated by rotation to remove the solvent and produce 10.7 g of a product in a yield of 100%, which was directly used in the next reaction without purification.

Workup

  1. additionAfter the completion of dropwise addition
  2. customThe resulting clear solution was evaporated by rotation
  3. customto remove the solvent

Sources & evidence

ORD record
ord-8572312555014b4289f541dd043f6305
Source dataset
uspto-grants-2016_04
Patent number
US09315438B2

Reaction notes

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