o-Vanillin → 2-(4-Chloro-3-nitrobenzoyl)-7-methoxybenzo[b]furan

HRID 263300Notes

Reaction equation

HRID 263300 reaction equation
[OH-].[K+].[OH:3][C:4]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O.Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([N+:25]([O-:27])=[O:26])[CH:19]=1)=[O:17]>CO>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]([C:15]2[O:3][C:4]3[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:5]=3[CH:6]=2)=[O:17])=[CH:19][C:20]=1[N+:25]([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 8991o-VanillinHCID 14797Potassium HydroxideHCID 27783302-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-one

Product 1

HCID 213165722-(4-Chloro-3-nitrobenzoyl)-7-methoxybenzo[b]furan

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2 g KOH are dissolved in 50 ml methanol, a solution of 5.4 g 2-hydroxy-3-methoxybenzaldehyde is added and subsequently a suspension of 10 g 2-bromo-4'-chloro-3'-nitroacetophenone in 75 ml methanol. The batch is refluxed for 6 hours, agitation is continued overnight at room temperature, and the crystals are suction-filtered. M.p. 136° C. (from ethyl acetate).

Workup

  1. temperatureThe batch is refluxed for 6 hours
  2. filtrationthe crystals are suction-filtered

Sources & evidence

ORD record
ord-7d340f095cd9431785b78c7db3008a04
Source dataset
uspto-grants-1979_05
Patent number
US04156732

Reaction notes

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