Thionyl Chloride → 2-Chloro-4-iodobenzoyl chloride

HRID 2172856Notes

Reaction equation

HRID 2172856 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:14])=O>>[Cl:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 8212642-Chloro-4-iodobenzoic Acid

Product 1

HCID 190815362-Chloro-4-iodobenzoyl chloride

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chloro-4-iodo-benzoic acid (470 mg) in thionyl chloride (6 mL) was stirred at 60° C. for 3 h. The excess thionyl chloride was removed in vacuo. The residue was washed with ether and dried to afford 2-chloro-4-iodo-benzoyl chloride (0.5 g), which was used directly in the next step where it was dissolved in 1,4-dioxane (10 mL). Phosphoryl chloride (5 mL) and IId (246 mg) were added, and the mixture was stirred at 90° C. for 1.5 h. The volatiles were removed in vacuo. The residue was partitioned between water and DCM. The organic layer was washed with sat. aq. NaHCO3, dried over NaSO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluent: pentane:EtOAc 10:1 to 5:1) to afford example Id7 (250 mg). LC/MS (method WXE-AB10): RT(PDA)=2.26 min; PDA/ELS purities 99%/99%; mass observed 422.0.

Workup

  1. customThe excess thionyl chloride was removed in vacuo
  2. washThe residue was washed with ether
  3. customdried

Sources & evidence

ORD record
ord-0dd1a2a9309b418683fc54695d6cdb71
Source dataset
uspto-grants-2015_06
Patent number
US09056863B2

Reaction notes

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