Dimethylformamide → 2,4-Difluoro-5-iodobenzoyl chloride

HRID 1670793Notes

Reaction equation

HRID 1670793 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([I:12])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:15])=O.CN(C=O)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([I:12])=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 111297952,4-Difluoro-5-iodobenzoic acid

Product 1

HCID 577339872,4-Difluoro-5-iodobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 11 (74.0 g, 260 mmol) in toluene (370 mL) was added thionyl chloride (95 mL, 1300 mmol) in DMF (2.5 mL, 26 mmol) and the mixture was heated to reflux for 4 h. The mixture was cooled to approximately 60° C. and filtered to remove insoluble material. The filtrate was concentrated under reduced pressure and residual thionyl chloride was co-evaporated with toluene (2×120 mL) to give crude 12 which was used without purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. filtrationfiltered
  4. customto remove insoluble material
  5. concentrationThe filtrate was concentrated under reduced pressure and residual thionyl chloride
  6. customto give crude 12 which
  7. customwas used without purification

Sources & evidence

ORD record
ord-c4d12b2e96734e9aa9427c510d143ef6
Source dataset
uspto-grants-2011_08
Patent number
US07994194B2

Reaction notes

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