Thiophosgene → HCID 13563672, compound

HRID 979724Notes

Reaction equation

HRID 979724 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([CH3:12])([CH3:11])[CH3:10].[C:13](Cl)([Cl:15])=[S:14].[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:15][C:13]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:4]=1)=[S:14]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 14798Sodium HydroxideHCID 10998772HCID 10998772, compound

Product 1

HCID 13563672HCID 13563672, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 50 ml of chloroform were dissolved 11.5 g of 4-bromo-3-tert-butylphenol and 6.5 g of thiophosgene, and 60 ml of 1-N sodium hydroxide aqueous solution were added dropwise thereto with stirring at room temperature. After completion of this dropwise addition, the mixture was subjected to stirring over a period of 3 hours at room temperature. From the reaction mixture was separated chloroform layer, which was thereafter dried over anhydrous calcium chloride and then chloroform was distilled off therefrom. The residue was purified through a column chromatography (employing silica gel as carrier and hexane as developing solvent) to give 10.3 g of O-4-bromo-3-tert-butylphenyl chlorothioformate.

Workup

  1. additionwere added dropwise
  2. additionAfter completion of this dropwise addition
  3. stirringto stirring over a period of 3 hours at room temperature
  4. customFrom the reaction mixture was separated chloroform layer, which
  5. dry with materialwas thereafter dried over anhydrous calcium chloride
  6. distillationchloroform was distilled off
  7. customThe residue was purified through a column chromatography (employing silica gel as carrier and hexane as developing solvent)

Sources & evidence

ORD record
ord-cb0cf84b9a0d45358d62287b9c878066
Source dataset
uspto-grants-1987_05
Patent number
US04668831

Reaction notes

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