Thiophosgene → Pentafluorophenyl 4-[(chlorocarbonothioyl)oxy]benzoate

HRID 231962Notes

Reaction equation

HRID 231962 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:23]=[CH:22][C:7]([C:8]([O:10][C:11]2[C:16]([F:17])=[C:15]([F:18])[C:14]([F:19])=[C:13]([F:20])[C:12]=2[F:21])=[O:9])=[CH:6][CH:5]=1.[C:24](Cl)([Cl:26])=[S:25]>O.C(Cl)(Cl)Cl>[Cl:26][C:24]([O:3][C:4]1[CH:23]=[CH:22][C:7]([C:8]([O:10][C:11]2[C:12]([F:21])=[C:13]([F:20])[C:14]([F:19])=[C:15]([F:18])[C:16]=2[F:17])=[O:9])=[CH:6][CH:5]=1)=[S:25]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 14798Sodium HydroxideHCID 20031799HCID 20031799, compound

Product 1

HCID 53892314Pentafluorophenyl 4-[(chlorocarbonothioyl)oxy]benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 1.34 g of sodium hydroxide in water was added dropwise over 15 minutes with vigorous stirring to a solution of 8.5 g of pentafluorophenyl 4-hydroxybenzoate and 3.2 ml of thiophosgene in 100 ml of chloroform at -20° C. The mixture was stirred at 5° C. until the reaction was complete and the organic layer separated, dried over calcium chloride and the solvent evaporated. Chromatography of the residue on silica gel eluting with hexane/ethyl acetate mixtures afforded 5.9 g of the title compound.

Workup

  1. customthe organic layer separated
  2. dry with materialdried over calcium chloride
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-e3180014867b4f0284f3c781d54dda64
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

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