HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Bromine → p-Nitrobenzyl 2-(4-bromo-2-azetidinon-1-yl)-2-(4-hydroxy-1,3-dithiolan-2-ylidene)acetate

HRID 980967
Notes
Print preview

Reaction equation

HRID 980967 reaction equation
[OH:1][CH:2]1[CH2:6][S:5][C:4](=[C:7]([N:21]2[CH:24](SC)[CH2:23][C:22]2=[O:27])[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[O:9])[S:3]1.[Br:28]Br>O1CCCC1.C(Cl)(Cl)(Cl)Cl>[Br:28][CH:24]1[N:21]([C:7](=[C:4]2[S:3][CH:2]([OH:1])[CH2:6][S:5]2)[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[O:9])[C:22](=[O:27])[CH2:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24408BromineHCID 86741253p-Nitrobenzyl 2-(4-hydroxy-1,3-dithiolan-2-ylidene)-2-(4-methylthio-2-azetidinon-1-yl)acetate

Product 1

HCID 53688010p-Nitrobenzyl 2-(4-bromo-2-azetidinon-1-yl)-2-(4-hydroxy-1,3-dithiolan-2-ylidene)acetateYield 99.8%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

p-Nitrobenzyl 2-(4-hydroxy-1,3-dithiolan-2-ylidene)-2-(4-methylthio-2-azetidinon-1-yl)acetate (121 mg) was dissolved in tetrahydrofuran (1 ml). A solution of bromine (45.2 mg) in carbon tetrachloride was added dropwise to the resulting solution, with ice cooling. The mixture was stirred at that temperature for 10 minutes and then the solvent was distilled off under reduced pressure and the resulting residue was purified by column chromatography (eluent: a 1:1 by volume mixture of benzene and ethyl acetate), to give 130 mg of the desired product.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customthe resulting residue was purified by column chromatography (eluent
  3. additiona 1:1 by volume mixture of benzene and ethyl acetate),

Sources & evidence

ORD record
ord-d83e03a6e9cd4fba955ff93dc999ff0c
Source dataset
uspto-grants-1987_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04639441

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes