Oxalyl chloride → 2-Fluoro-5-iodobenzoyl chloride

HRID 528789Notes

Reaction equation

HRID 528789 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:15])=O>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27789252-Fluoro-5-iodobenzoic acid

Product 1

HCID 27782042-Fluoro-5-iodobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-fluoro-5-iodobenzoic acid (Aldrich, 5.27 g, 19.8 mmol) in CH2Cl2 (35.0 mL) was added oxalyl chloride (14.9 mL, 29.7 mmol, 1M solution in CH2Cl2) followed by 2 drops of DMF via syringe. Gas evolution was initiated and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was then quenched with sat. aq. NH4Cl solution and extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to give crude 2-fluoro-5-iodobenzoyl chloride which was used directly in the next step.

Workup

  1. customThe reaction mixture was then quenched with sat. aq. NH4Cl solution
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b9afd51c76140b6baba954df9877faa
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

Loading…