Oxalyl chloride → 2-Chloro-5-iodobenzoyl chloride

HRID 718212Notes

Reaction equation

HRID 718212 reaction equation
[Cl: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>CN(C=O)C.C(Cl)Cl>[Cl: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 5196382-Chloro-5-iodobenzoic acid

Product 1

HCID 47693022-Chloro-5-iodobenzoyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
12.5 °C

Procedure

A 1 L 4-necked flask equipped with thermometer and mechanical stirrer (operating at 150 RPM) was charged with 2-chloro-5-iodobenzoic acid (14.1 g, 0.05 mol), DCM (70.5 mL) and oxalyl chloride (5.5 mL, 0.06 mol). After stirring for 10 min, the mixture was cooled to 10 to 15° C. and DMF (0.15 mL, 1.92 mmol) was added by syringe over 10 min in two bolus of 0.1 and 0.05 mL while keeping the reaction temperature below 20° C. After the addition was completed, the mixture was warmed to 25° C. and stirred for 16 h. The mixture was concentrated and the residue was dried under vacuum at 30° C. for 5 h to give 15.0 g of product as a white solid. Yield: 100%. LCMS-0013: 99% Purity. 1H NMR (CDCl3, 400 MHz): 8.33 (d, J=2.4 Hz, 1H), 7.81˜7.84 (dd, J=2.4 Hz, 8.4 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H).

Workup

  1. customA 1 L 4-necked flask equipped with thermometer and mechanical stirrer (operating at 150 RPM)
  2. customthe reaction temperature below 20° C
  3. additionAfter the addition
  4. temperaturethe mixture was warmed to 25° C.
  5. stirringstirred for 16 h
  6. concentrationThe mixture was concentrated
  7. customthe residue was dried under vacuum at 30° C. for 5 h

Sources & evidence

ORD record
ord-c4bf134c9f084ba485541cba495e2979
Source dataset
uspto-grants-2015_11
Patent number
US09193751B2

Reaction notes

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