Bromide ion → HCID 9957458, compound

HRID 1455881Notes

Reaction equation

HRID 1455881 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[C:10](=[C:27]([CH3:29])[CH3:28])[N:11]1[C:14](=[O:15])[C:13]([Br:17])([Br:16])[CH:12]1S(C1C=C(C)ON=1)(N)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:31]Br.[Br-]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:30])[C:10](=[C:27]([CH3:29])[CH3:28])[N:11]1[C:14](=[O:15])[C:13]([Br:17])([Br:16])[CH:12]1[Br:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 259Bromide ionHCID 24408BromineHCID 178447472HCID 178447472, compound

Product 1

HCID 9957458HCID 9957458, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3,3-dibromo-alpha-(1-methylethylidene)-2-[(5-methyl-isoxazole-3-yl)-aminosulfinyl]-4-oxo-1-azetidine acetic acid benzyl ester (5.61 g; 0.01 mole) was dissolved in chloroform (120 mL), bromine on a polymer carrier (12.5 g; the content of bromide bound to the polymer matrix with polyvinylpyrrolidone was 26%, 0.02 mole) (prepared according to J. Johar, M. Zupan and B. Sket, J. Chem. Soc. Perkin Trans. I, 2059, (1982)) was added and it was stirred for 12 hours at room temperature. The polymer was sucked off and the filtrate was evaporated to dryness. The obtained product was passed through a Merck 60 silica gel column with methylene chloride and thereafter 2,3,3-tribromo-alpha-(1-methylethylidene)-4-oxo-1-azetidine acetic acid benzyl ester (2.36 g, 47.6%) was isolated, m.p. 68°-70° C.

Workup

  1. custom(prepared according to J. Johar, M. Zupan and B. Sket, J. Chem. Soc. Perkin Trans. I, 2059, (1982))
  2. additionwas added
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-c1dc43c79d464e67a6166edd63c8c448
Source dataset
uspto-grants-1998_12
Patent number
US05843939

Reaction notes

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