Bromine → HCID 178488960, compound

HRID 1722015Notes

Reaction equation

HRID 1722015 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Br:19]Br.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Br:19][C:12]1[NH:11][C:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=2)=[N:14][C:13]=1[C:15]([F:16])([F:17])[F:18]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 178488962HCID 178488962, compound

Product 1

HCID 178488960HCID 178488960, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a suspension of 55 (2.56 g, 0.0092 mol) in CHCl3 (75ml) was added dropwise with stirring a solution of bromine (1.55 g, 0.0096 mol) in CHCl3 (75 ml). After stirring for 3 days, saturated NaHCO3 was added, the layers separated and the aqueous layer extracted with CHCl3 (2 x). The organic extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product eluted with 1.5% CH3OH-CHCl3 to yield 2.25 g (69%) of 56, m.p. 228.30° C. (CHCl3). Analysis calculated for C11H7BrClF3N2O.

Workup

  1. additionwas added dropwise
  2. customthe layers separated
  3. extractionthe aqueous layer extracted with CHCl3 (2 x)
  4. customThe organic extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was chromatographed on silica gel
  8. washthe product eluted with 1.5% CH3OH-CHCl3

Sources & evidence

ORD record
ord-08f3b4fffcbc41e3ac9cac34490a3f64
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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