Dichloromethane → 2-Chloro-5-iodobenzoyl chloride

HRID 2067774Notes

Reaction equation

HRID 2067774 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].[Cl:12]CCl.C(Cl)(=O)C(Cl)=O>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([Cl:12])=[O:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chloride2×HCID 5196382-Chloro-5-iodobenzoic acid

Product 1

HCID 47693022-Chloro-5-iodobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 2 L three-necked round bottom flask with mechanical stirrer, rubber septum with temperature probe and pressure-equalized addition funnel with gas bubbler was charged with 2-chloro-5-iodobenzoic acid (199.41 g, 0.706 mol), dichloromethane (1.2 L, KF=0.003 wt % water) and the suspension was set stirring at ambient temperature. Then N,N-dimethylformamide (0.6 mL, 1.1 mol %) was added followed by oxalyl chloride (63 mL, 0.722 mol, 1.02 equiv) which was added over 11 min. The reaction was allowed to stir at ambient overnight and became a solution. After 18.75 hours, additional oxalyl chloride (6 mL, 0.069 mol, 0.10 equiv) was added to consume unreacted starting material. After 2 hours, the reaction mixture was concentrated in vacuo to afford crude 2-chloro-5-iodobenzoyl chloride as a pale yellow foam which will be carried forward to the next step.

Workup

  1. additionwas added over 11 min
  2. stirringto stir at ambient overnight
  3. customto consume unreacted
  4. waitAfter 2 hours
  5. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-c934165d87eb4491a1b91d48e583a097
Source dataset
uspto-grants-2012_10
Patent number
US08293878B2

Reaction notes

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