Iodine → 2,5-Dichloro-3-iodobenzoic acid

HRID 2292457Notes

Reaction equation

HRID 2292457 reaction equation
[I:1]I.N(OC(C)(C)C)=O.N[C:11]1[C:12]([Cl:21])=[C:13]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[C:14]([OH:16])=[O:15].N(OCCCC)=O>CS(C)=O.O>[Cl:21][C:12]1[C:11]([I:1])=[CH:19][C:18]([Cl:20])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 807Iodine2×HCID 8630ChlorambenHCID 10906Tert-Butyl nitriteHCID 10996Butyl nitrite

Product 1

HCID 214781212,5-Dichloro-3-iodobenzoic acidYield 84.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

In a flask 48.35 grams (0.191 mole) of iodine was dissolved in 90 mL of dimethyl sulfoxide. To this solution was added 29.47 grams (0.286 mole) of tertiary butyl nitrite. A solution of 39.25 grams (0.191 mole) of 3-amino-2,5-dichlorobenzoic acid in 130 mL of dimethyl sulfoxide was added dropwise to the solution of iodine and butyl nitrite. During this addition the temperature rose from 20° C. to 50° C., at which temperature the addition was stopped until the reaction mixture had cooled to 35° C. The addition was then completed. When the addition was complete, the reaction mixture was stirred for approximately 16 hours, then poured into water, and this mixture was extracted with ethyl acetate. The extracts were combined and washed with an aqueous solution of sodium hydrogen sulfite and finally with water. The combined extracts were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated from the filtrate under reduced pressure, yielding 51.34 grams of 2,5-dichloro-3-iodobenzoic acid as a solid.

Workup

  1. additionDuring this addition the temperature
  2. customrose from 20° C. to 50° C., at which temperature
  3. additionthe addition
  4. additionThe addition
  5. additionWhen the addition
  6. extractionthis mixture was extracted with ethyl acetate
  7. washwashed with an aqueous solution of sodium hydrogen sulfite and finally with water
  8. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe solvent was evaporated from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-4d910e66d9734a9c8653a060b46bed70
Source dataset
uspto-grants-1997_11
Patent number
US05683966

Reaction notes

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