Bromine → HCID 12811227, compound

HRID 1446960Notes

Reaction equation

HRID 1446960 reaction equation
C(=O)(O)[O-].[Na+].[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2[NH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:18]=2)[CH:10]=[C:11]([Cl:13])[CH:12]=1.[Br:23]Br.CC(C)=O.CCCCCC>O.C(Cl)(Cl)Cl>[Br:23][C:17]1[N:18]=[C:14]([C:9]2[CH:10]=[C:11]([Cl:13])[CH:12]=[C:7]([Cl:6])[CH:8]=2)[NH:15][C:16]=1[C:19]([F:20])([F:22])[F:21]

Participants

8

Reactant 4

HCID 24408Bromine2×HCID 516892Sodium BicarbonateHCID 20551868HCID 20551868, compoundHCID 21880519Acetone hexane

Product 1

HCID 12811227HCID 12811227, compound

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Sodium bicarbonate is made into a paste by adding a few drops of water to 1.5 g (9.4 mol). The 2-(3,5-dichlorophenyl)-5-trifluoromethylimidazole is dissolved in 100 ml chloroform and added to the flask containing the paste. 1.5 g of bromine is added and stirred. TLC on alumina using 50:50 acetone-hexane clearly differentiates starting material from product. Additional bromine is added until starting material is no longer present (0.1 g). Water is added and the organic phase removed. The layer is washed with sodium bisulfite, brine and dried over sodium sulfate. The organic phase is stripped and the residue taken up in 1:1 ether hexane and filtered through silica gel.

Workup

  1. additionadded to the flask
  2. additioncontaining the paste
  3. customthe organic phase removed
  4. washThe layer is washed with sodium bisulfite, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-560973628fe344eebc7db843f61253ef
Source dataset
uspto-grants-1982_02
Patent number
US04314844

Reaction notes

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