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4-Bromophenol → (7aS,6S)-2-(3,5-dichloro-phenyl)-6-(4-bromophenoxy)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione

HRID 49981
Notes
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Reaction equation

HRID 49981 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@H:12]3[CH2:15][C@@H:16]([OH:18])[CH2:17][N:11]3[C:10]2=[O:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Br:39][C:40]1[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@H:12]3[CH2:15][C@H:16]([O:18][C:43]4[CH:44]=[CH:45][C:40]([Br:39])=[CH:41][CH:42]=4)[CH2:17][N:11]3[C:10]2=[O:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58840802(6R,7aS)-2-(3,5-dichlorophenyl)-6-hydroxytetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione

Product 1

HCID 9804074(7aS,6S)-2-(3,5-dichloro-phenyl)-6-(4-bromophenoxy)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione
Yield 6.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (7aS,6R)-2-(3,5-dichloro-phenyl)-6-hydroxy-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione (0.5 g) (1.67 mmol) (Preparation 2), Ph3P (0.44 g) (1eq.) and 4-bromophenol (0.29 g) (1 eq.) in 5 mL of dry THF at 0° C. was added DIAD (0.337 g) in a minimal volume of THF. The reaction mixture was warmed to RT overnight. After evaporating the solvent, the residue was dissolved in DCM, washed with NaHCO3 solution, water, dried over MgSO4, and the solvent was evaporated under reduced pressure, to afford after SiO2 chromatography (eluent: DCM) the titled compound as a white solid (50 mg). Mp=116° C. NMR (DMSO, 200 MHz): 7.75 (1H, m), 7.5-7.4 (4H, d+d), 6.85 (2H, d), 5.1 (1H, m), 4.6 (1H, dd), 3.95 (1H, dd), 3.35 (1H, dd), 2.7-2.5 (1H, m), 2.25 (1H, bd).

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with NaHCO3 solution, water
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0b773038a2204702ba39139d0698cd2b
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06710064B2

Reaction notes

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