Water → HCID 12531896, compound

HRID 1863291Notes

Reaction equation

HRID 1863291 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH:7]([C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[C:21]1([SH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH:7]([C:12]2[CH:17]=[CH:16][C:15]([S:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:14][CH:13]=2)[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7969ThiophenolHCID 20392611HCID 20392611, compound

Product 1

HCID 12531896HCID 12531896, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 6.04 g of methyl α-(p-chlorophenoxy)(p-iodophenyl)acetate, 3.36 g of cuprous phenylmercaptide, and 800 mg of thiophenol in 150 ml of pyridine is heated under Argon overnight. The mixture is poured into 300 ml of water and extracted with two 100 ml portions of chloroform. The combined organic layers are washed with two 50 ml portions of 5% NaOH, two 50 ml portions of water, 50 ml of saturated brine and dried over MgSO4. Evaporation of the solvent at reduced pressure yields an oil. After column chromatography (benzene) and bulb-to-bulb distillation (173° C. @ 0.01 mm) there is obtained the product as a yellow oil.

Workup

  1. temperatureis heated under Argon overnight
  2. extractionextracted with two 100 ml portions of chloroform
  3. washThe combined organic layers are washed with two 50 ml portions of 5% NaOH, two 50 ml portions of water, 50 ml of saturated brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent at reduced pressure
  6. customyields an oil
  7. distillationAfter column chromatography (benzene) and bulb-to-bulb distillation (173° C. @ 0.01 mm) there

Sources & evidence

ORD record
ord-272e11fdc1e64e17b4cdbe4a671aa2db
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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