N-bromobutanimide → HCID 53964107, compound

HRID 1413069Notes

Reaction equation

HRID 1413069 reaction equation
[C:1]([O:4][C@H:5]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:38])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:29])[CH2:16][CH2:17][CH2:18][C:19]([OH:28])([C:24]([F:27])([F:26])[F:25])[C:20]([F:23])([F:22])[F:21])[CH2:6]1)(=[O:3])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C@H:5]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C:7](=[CH:8][CH:9]=[C:10]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:38])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:29])[CH2:16][CH2:17][CH2:18][C:19]([OH:28])([C:24]([F:25])([F:26])[F:27])[C:20]([F:23])([F:21])[F:22])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 53848303HCID 53848303, compound

Product 1

HCID 53964107HCID 53964107, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a refluxing solution of the acetate 4 (19 mg) in CCl4 (2 ml), N-bromosuccinimide (9 mg) was added and the mixture was refluxed for 20 min under argon. After cooling, the resulting precipitate was filtered off, and the filtrate was evaporated under vacuo. The residue was dissolved in xylene (1.5 ml) and dropped into a refluxing solution of s-collidine (0.5 ml) in xylene (1.5 ml). After refluxing for 10 min, the mixture was extracted with ethyl acetate. The crude product was dissolved in acetone (5 ml) and treated with p-toluenesulfonic acid (10 mg) by stirring for 14 hr at room temperature. After addition of water, the mixture was extracted with ethyl acetate. The reaction product was purified with preparative TLC (benzene-ethyl acetate, 50:1; two times) to give the 5,7-diene 5 (4.9 mg); UV, λMax (EtOH)262(sh), 271, 282, 293 nm.

Workup

  1. temperaturethe mixture was refluxed for 20 min under argon
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate was filtered off
  4. customthe filtrate was evaporated under vacuo
  5. dissolutionThe residue was dissolved in xylene (1.5 ml)
  6. additiondropped into a refluxing solution of s-collidine (0.5 ml) in xylene (1.5 ml)
  7. temperatureAfter refluxing for 10 min
  8. extractionthe mixture was extracted with ethyl acetate
  9. dissolutionThe crude product was dissolved in acetone (5 ml)
  10. additiontreated with p-toluenesulfonic acid (10 mg)
  11. additionAfter addition of water
  12. extractionthe mixture was extracted with ethyl acetate
  13. customThe reaction product was purified with preparative TLC (benzene-ethyl acetate, 50:1; two times)

Sources & evidence

ORD record
ord-504d37eea5c04ccc9954020b69d8e1ed
Source dataset
uspto-grants-1981_02
Patent number
US04248791

Reaction notes

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