Bromine → HCID 12811226, compound

HRID 1446962Notes

Reaction equation

HRID 1446962 reaction equation
C(=O)(O)[O-].[Na+].[F:6][C:7]1[C:12]([F:13])=[C:11]([F:14])[C:10]([F:15])=[C:9]([F:16])[C:8]=1[C:17]1[NH:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][N:21]=1.[Br:26]Br.CC(C)=O.CCCCCC>O.C(Cl)(Cl)Cl>[Br:26][C:20]1[N:21]=[C:17]([C:8]2[C:9]([F:16])=[C:10]([F:15])[C:11]([F:14])=[C:12]([F:13])[C:7]=2[F:6])[NH:18][C:19]=1[C:22]([F:25])([F:24])[F:23]

Participants

8

Reactant 4

HCID 24408Bromine2×HCID 516892Sodium BicarbonateHCID 20551774HCID 20551774, compoundHCID 21880519Acetone hexane

Product 1

HCID 12811226HCID 12811226, 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-(2,3,4,5,6-pentafluorophenyl)-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-29eb7d0eee774aeb95f584fe03726256
Source dataset
uspto-grants-1982_02
Patent number
US04314844

Reaction notes

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