Nitrosobenzene → HCID 25115715, compound

HRID 1099330Notes

Reaction equation

HRID 1099330 reaction equation
C1CCN2C(=NCCC2)CC1.[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.[N:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]>ClCCl>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]([N:21]([OH:22])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11473NitrosobenzeneHCID 707414-BromobenzaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 25115715HCID 25115715, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DBU (3.8 mg, 0.025 mmol) was added under argon to a solution of 4-bromobenzaldehyde (185 mg, 1 mmol), nitrosobenzene (107 mg, 1 mmol) and catalyst (1.82 mg, 0.005 mmol) in dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 10 min. The solvent was removed under vacuum, and the residue was purified by flash silica gel column chromatography using hexane and ethyl acetate as the eluents.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-f540b9ad1a7b490b88f92cb27f4e3f2d
Source dataset
uspto-grants-2012_03
Patent number
US08143423B2

Reaction notes

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