Bromine → HCID 18399626, compound

HRID 381282Notes

Reaction equation

HRID 381282 reaction equation
[Br:1]Br.[C:3]([C:6]1[S:7][CH:8]=[C:9]([C:20]([O:22][CH3:23])=[O:21])[C:10]=1[O:11][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:5])[CH3:4]>ClC(Cl)(Cl)Cl>[Br:1][CH2:4][C:3]([C:6]1[S:7][CH:8]=[C:9]([C:20]([O:22][CH3:23])=[O:21])[C:10]=1[O:11][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 18399622HCID 18399622, compound

Product 1

HCID 18399626HCID 18399626, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
22.5 °C

Procedure

A solution of 1.28 mL of bromine in 24 mL of tetrachloromethane was added dropwise to a solution of 7.23 g of Compound 1C in 72 mL of tetrachloromethane over a period of 10 minutes and stirred at reflux. After a further 5 minutes at reflux, the mixture was cooled to 20-25° C. The precipitated solid was collected by filtration and washed with cold tetrachloromethane to yield 7 g (77%) of Compound 1D, melting at 115-118° C. The compound was contaminated with impurities 1B and methyl 2-(2,2-dibromoacetyl)-3-benzoyloxythiophene-4-carboxylate (2% and 6% mol. respectively, determined by 1H-NMR spectroscopy), but could be used without further purification in the next reaction step.

Workup

  1. temperatureat reflux
  2. temperatureAfter a further 5 minutes at reflux
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with cold tetrachloromethane

Sources & evidence

ORD record
ord-8075b056979041979cffd9c1ef79de22
Source dataset
uspto-grants-2001_10
Patent number
US06306861B1

Reaction notes

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