Triethylamine → 7-Nitrobenzofuran-3(2H)-one

HRID 440643Notes

Reaction equation

HRID 440643 reaction equation
[N+:1]([C:4]1[C:12]2[O:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].BrN1C(=[O:19])CCC1=O.BrC1C2C=CC=C([N+]([O-])=O)C=2OC=1.C(N(CC)CC)C>CS(C)=O.F[B-](F)(F)F.[Ag+]>[N+:1]([C:4]1[C:12]2[O:11][CH2:10][C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 128059492,3-Dihydro-7-nitrobenzofuranHCID 186797403-Bromo-7-nitrobenzofuran

Product 1

HCID 224047597-Nitrobenzofuran-3(2H)-one

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Schema 3 illustrates an alternative method of producing the above benzofuranyl-3-on-7-yl uracils by the oxidation of a 2,3-dihydro-4,6-optionally disubstituted-7-nitrobenzofuran (Compound III in Schema 1). The 2,3-dihydro-7-nitrobenzofuran is treated with N-bromosuccinimide while being irradiated with light. The product of this reaction, a 3-bromo-7-nitrobenzofuran (VIII), is then reacted with silver tetrafluoroborate in dimethyl sulfoxide in the presence of triethylamine, yielding the corresponding 2,3-dihydro-7-nitrobenzofuran- 3-one (IX). This compound may be used in place of compound III in Schema I to produce the corresponding 3-(2,3-dihydrobenzofuran-3-on-7-yl)-1-alkyl-6-haloalkyluracil.

Workup

  1. customwhile being irradiated with light
  2. customThe product of this reaction

Sources & evidence

ORD record
ord-12a3159a4d0a476db1270e7c5fd912f7
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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