Thionyl Chloride → 2-iodo-3-methyl-benzoyl Chloride

HRID 723089Notes

Reaction equation

HRID 723089 reaction equation
[I:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:14])=O>C1COCC1>[I:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27593652-Iodo-3-methylbenzoic acid

Product 1

HCID 110332772-iodo-3-methyl-benzoyl Chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-iodo-3-methyl benzoic acid (1310 mg, 5 mmol) and thionyl chloride (730 μL, 10 mmol) were dissolved into THF (10 mL) and stirred at RT for 4 days. The solvents were removed in vacuo and the resulting residue was dissolved into EtOAc, washed with brine. The combined organic layers were dried (MgSO4) and the solvents were removed in vacuo resulting in an oil that was used without further purification or characterization.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe resulting residue was dissolved into EtOAc
  3. washwashed with brine
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customthe solvents were removed in vacuo
  6. customresulting in an oil that
  7. customwas used without further purification or characterization

Sources & evidence

ORD record
ord-53c7ae3ca1094e579bf31dbcc65d4c5b
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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