N-bromobutanimide → HCID 67813348, compound

HRID 2401367Notes

Reaction equation

HRID 2401367 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[C:14]([CH3:15])=[C:13]([CH3:16])[S:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>CN(C=O)C>[Br:17][C:11]1[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=1[C:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)=[O:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67812940HCID 67812940, compound

Product 1

HCID 67813348HCID 67813348, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-chlorophenyl)(4,5-dimethylthiophen-3-yl)methanone (1.99 g, 7.94 mmol) in DMF (15 mL) was added N-bromosuccinimide (1.55 g, 8.71 mmol) in one portion. After 2 h, the reaction mixture was partitioned between water and MTBE. The aqueous layer was extracted with MTBE and the combined organic layer was washed with 1% sodium thiosulfate, water, dried over Na2SO4 and concentrated to give light yellow solids. The resultant solids was purified on Biotage system (gradient elution 1% EtOAc:99% Hexanes to 4% EtOAc:96% Hexanes) to give the titled compound as yellow solids (2.40 g, 7.28 mmol, 92% yield). LC/MS m/z 329 [(M (35Cl, 79Br)+H]+ and m/z 331 [M+H]+.

Workup

  1. customthe reaction mixture was partitioned between water and MTBE
  2. extractionThe aqueous layer was extracted with MTBE
  3. washthe combined organic layer was washed with 1% sodium thiosulfate, water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give light yellow solids
  7. customThe resultant solids was purified on Biotage system (gradient elution 1% EtOAc:99% Hexanes to 4% EtOAc:96% Hexanes)

Sources & evidence

ORD record
ord-832c0563812845968eb9d713c9174493
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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