N-bromobutanimide → HCID 54144625, compound

HRID 1248663Notes

Reaction equation

HRID 1248663 reaction equation
BrN1C(=O)CCC1=O.[CH2:9]([CH:16]1[CH:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:19][C:18](=[O:28])[O:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)(Cl)Cl.[W]>[CH:21](=[C:20]1[C:16](=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:17][C:18](=[O:28])[O:19]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 20277501HCID 20277501, compound

Product 1

HCID 54144625HCID 54144625, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (0.1033 g, 0.58 mmole) was added to a refluxing solution of 4,5-dibenzyl-1,3-dioxolan-2-one (75 mg, 0.28 mmole) in CCl4 (30 ml) under argon. The refluxing mixture was irradiated with a 75 watt unfrosted tungsten light for 0.5 h. Refluxing was continued for 3 h, then the solution was cooled, filtered, and the solvent removed in vacuo (20° C./15 mm Hg). Flash chromatography (ethyl ether-hexane eluent) gave 4,5-dibenzylidene-1,3-dioxolan-2-one (47 mg, 63%): mp115° C. (rapid heating); IR (AgCl) 3023, 1812, 1493, 1453, 1365, 1156, 1087, 910, 697 cm-1 ; 'H NMR (CDCl3) 7.39(s, 10H), 4.95(s, 2H).

Workup

  1. temperatureRefluxing
  2. temperaturethe solution was cooled
  3. filtrationfiltered
  4. customthe solvent removed in vacuo (20° C./15 mm Hg)

Sources & evidence

ORD record
ord-5efafcc331394fb7bce2cb835574c558
Source dataset
uspto-grants-1985_06
Patent number
US04525540

Reaction notes

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