Iodine chloride → 6-Chloro-2,4-difluoro-3-iodobenzaldehyde

HRID 2249386Notes

Reaction equation

HRID 2249386 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([Si](C)(C)C)=[C:4]([F:15])[CH:3]=1.[I:16]Cl>C(Cl)Cl>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([I:16])=[C:4]([F:15])[CH:3]=1

Participants

4

Reactant 2

HCID 24640Iodine chloride2×HCID 866138416-Chloro-2,4-difluoro-3-trimethylsilylbenzaldehyde

Product 1

HCID 866138426-Chloro-2,4-difluoro-3-iodobenzaldehydeYield 162.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-chloro-2,4-difluoro-3-trimethylsilylbenzaldehyde (600 mg, 2.4 mmol) in methylene chloride (7 mL) was cooled to 0° C. and treated with solution of iodochloride (780 mg, 4.8 mmol) in methylene chloride (10 ML) and stirred at ambient temperature for 2 hours. Additional iodochloride (900 mg) was added and the solution heated under reflux for 40 minutes. The solution was allowed to cool and was washed with sodium bisulfite (15 ml, 5% solution), water (10 mL), and a saturated solution of sodium bicarbonate (10 mL). The organic phase was dried (sodium sulfate) and concentrated to give 6-chloro-2,4-difluoro-3-iodobenzaldehyde (620 mg, 3.9 mmol): LC/MS (m/z=302).

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 40 minutes
  3. temperatureto cool
  4. washwas washed with sodium bisulfite (15 ml, 5% solution), water (10 mL)
  5. dry with materialThe organic phase was dried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dd417c1a47be4b668b2ecf87abceb1f9
Source dataset
uspto-grants-2008_01
Patent number
US07314849B2

Reaction notes

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