N-bromobutanimide → 3-Bromo-2-(pyridin-4-yl)-1-oxaspiro[4.4]non-2-en-4-one

HRID 655474Notes

Reaction equation

HRID 655474 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[C:10](=[O:12])[CH:11]=2)=[CH:3][CH:2]=1.C1C(=O)N([Br:24])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:24][C:11]1[C:10](=[O:12])[C:9]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[O:8][C:7]=1[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 593547772-(Pyridin-4-yl)-1-oxaspiro[4.4]non-2-en-4-one

Product 1

HCID 593548103-Bromo-2-(pyridin-4-yl)-1-oxaspiro[4.4]non-2-en-4-oneYield 72.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of afford 2-(pyridin-4-yl)-1-oxaspiro[4.4]non-2-en-4-one (0.18 g, 0.84 mmol) in CHCl3 (10 mL) was added NBS (0.22 g, 1.25 mmol) portionwise at RT and the reaction mixture was stirred for 1 h. The reaction mixture was diluted with DCM (30 mL), washed with water (10 mL), brine (10 mL), dried over Na2SO4, filtered and then concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 3-bromo-2-(pyridin-4-yl)-1-oxaspiro[4.4]non-2-en-4-one (0.18 g, 40%) as an oil.

Workup

  1. washwashed with water (10 mL), brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto obtain the crude product
  6. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-06debe4600884fedb3510d2b4ffa9920
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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