Bromine → HCID 18930383, compound

HRID 129642Notes

Reaction equation

HRID 129642 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:18]([F:21])([F:20])[F:19])=[CH:11][C:12]=2[S:13][C:14]([F:17])([F:16])[F:15])=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:27]Br>C(O)(=O)C.C(OCC)(=O)C.O>[Br:27][C:11]1[C:12]([S:13][C:14]([F:16])([F:17])[F:15])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:9][C:10]=1[C:18]([F:21])([F:19])[F:20]

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 18930386HCID 18930386, compound

Product 1

HCID 18930383HCID 18930383, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 22728543Water ethylacetateSolvent

Procedure

A solution of 2-(p-chlorophenyl)-5-(trifluoromethyl)-3-[(trifluoromethyl)thio]pyrrole (1.03 g, 3.0 mmol) and sodium acetate (0.3 g, 3.6 mmol) in acetic acid is treated with bromine (0.58 g, 3.6 mmol), stirred for 30 minutes at room temperature and diluted with an ethyl acetate/water mixture. The organic phase is separated, washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a semi-solid. Chromatography of the semi-solid using silica gel and hexanes gives the title product as a white solid (mp 87.0°-88.5° C.) which is identified by 1HNMR, 19FNMR and 13CNMR spectral analyses.

Workup

  1. customThe organic phase is separated
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a semi-solid

Sources & evidence

ORD record
ord-0a87e9588d7f41ab96d3bcded9a715e0
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Reaction notes

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