4-Nitrobenzyl bromide → HCID 85738246, compound

HRID 1459126Notes

Reaction equation

HRID 1459126 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:5]([CH:6]=O)[C:4]=1[OH:14].[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)([O-:17])=[O:16].N12CCCN=C1CCCCC2>O1CCOCC1>[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([C:22]2[O:14][C:4]3[C:3]([O:2][CH3:1])=[CH:10][C:9]([N+:11]([O-:13])=[O:12])=[CH:8][C:5]=3[CH:6]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 660114-Nitrobenzyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3078862-Hydroxy-3-methoxy-5-nitrobenzaldehyde

Product 1

HCID 85738246HCID 85738246, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

5.0 g (1.0 equivalent) of 3-methoxy-5-nitrosalicylaldehyde and 6.03 g (1.1 equivalents) of p-nitrobenzyl bromide were dissolved in 15 ml of 1,4-dioxane, and then 13.5 g (3.5 equivalents) of 1,8-diazabicyclo[5.4.0]undeca-7-ene was added thereto. The resulting mixture was heated at about 100° C. for three hours with stirring, and then cooled to room temperature. Thereafter, the resulting solid substance was filtered off and sufficiently washed with ethanol. Thus, 4.55 g of 2-(p-nitrophenyl)-5-nitro-7-methoxybenzo[b]furan was obtained (yield: 70%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThereafter, the resulting solid substance was filtered off
  3. washsufficiently washed with ethanol

Sources & evidence

ORD record
ord-c9a9a0a4cd594046bd5a44e768142206
Source dataset
uspto-grants-1998_12
Patent number
US05853930

Reaction notes

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