Iodine → HCID 21908075, compound

HRID 1247676Notes

Reaction equation

HRID 1247676 reaction equation
P.II.C([O:6][C:7](=[O:21])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=O)=O)=[CH:12][C:11]=1[Cl:20])C.O>C(O)(=O)C>[Cl:20][C:11]1[CH:12]=[C:13]([SH:16])[CH:14]=[CH:15][C:10]=1[O:9][CH2:8][C:7]([OH:21])=[O:6]

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 24404PhosphineHCID 15145183Ethyl (4-chlorosulfonyl-2-chloro-phenoxy)-acetate

Product 1

HCID 21908075HCID 21908075, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a refluxing solution of PH3 (17 g, 500 mmol) and I2 (2.4 g, 9.4 mmol) in glacial acetic acid (100 ml) was added slowly a solution of (4-chlorosulfonyl-2-chloro-phenoxy)-acetic acid ethyl ester (47.5 g, 151 mmol) in glacial acetic acid (1000 ml). The reaction mixture was refluxed for 24 h. Water (20 ml) was added carefully and the mixture was refluxed for further 1 h. After cooling, the reaction mixture was filtered and the filtrate diluted with water (500 ml). The mixture was extracted with dichloromethane (3×100 ml), and the organic phases were washed with water. After drying the dichloromethane phase was evaporated to give crude (2-chloro-4-mercapto-phenoxy)-acetic acid in 17 g yield.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. temperaturethe mixture was refluxed for further 1 h
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. additionthe filtrate diluted with water (500 ml)
  6. extractionThe mixture was extracted with dichloromethane (3×100 ml)
  7. washthe organic phases were washed with water
  8. dry with materialAfter drying the dichloromethane phase
  9. customwas evaporated

Sources & evidence

ORD record
ord-6bb96e95fd9c4f94a20c45c5e7e6c53a
Source dataset
uspto-grants-2006_10
Patent number
US07129268B2

Reaction notes

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