N-bromobutanimide → HCID 86725335, compound

HRID 925225Notes

Reaction equation

HRID 925225 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].C1C(=O)N([Br:26])C(=O)C1>C(#N)C>[Br:26][C:14]1[C:13]([OH:16])=[CH:12][C:9]2[CH2:10][CH2:11][N:5]([C:3](=[O:4])[C:2]([F:1])([F:17])[F:18])[CH2:6][CH2:7][C:8]=2[CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59730230HCID 59730230, compound

Product 1

HCID 86725335HCID 86725335, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Into a 100 ml flask, the product of step (d) (1.65 g, 6.37 mmol) dissolved in acetonitrile (25 ml) was added. To this stirred solution, NBS (1.07 g, 6.05 mmol) was added. The reaction mixture was heated to 80° C. for 15 minutes and then partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 40% EtOAc in hexanes) gave the sub-title compound as a yellow solid (1.4 g). MS: ESI (positive): 338, 340 (M+H).

Workup

  1. additionwas added
  2. custompartitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washThe combined EtOAc extracts were washed with brine
  5. dry with materialdried over Na2SO4, and solvent
  6. customevaporated in vacuo
  7. customto give the crude product
  8. customPurification
  9. washby silica-gel chromatography (gradient elution: 0 to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d4e5eb3ed0684e538a84a2e29ba1ad15
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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