Bromine → HCID 178488960, compound

HRID 235965Notes

Reaction equation

HRID 235965 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 (75 ml) 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×). 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).

Workup

  1. additionwas added dropwise
  2. customthe layers separated
  3. extractionthe aqueous layer extracted with CHCl3 (2×)
  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

Sources & evidence

ORD record
ord-53c047f727fa4e20b3ea19d969ff0036
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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