p-Fluoronitrobenzene → 2-Bromo-4-methoxy-3-(4-nitrophenoxy)benzaldehyde

HRID 2427849Notes

Reaction equation

HRID 2427849 reaction equation
[Br:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[OH-].[K+].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>CS(C)=O.O>[Br:1][C:2]1[C:9]([O:10][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 14797Potassium HydroxideHCID 2240112-Bromoisovanillin

Product 1

HCID 211057062-Bromo-4-methoxy-3-(4-nitrophenoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

2-Bromo-3-hydroxy-4-methoxy-benzaldehyde (15.0 g, 64.9 mmoles) is dissolved in DMSO (100 mL). Potassium hydroxide (4.01 g, 71.4 mmoles) and 1-Fluoro-4-nitro-benzene (13.74 g, 97.4 mmoles) are added to the solution. The reaction mixture is stirred at 130° C. for 3 hours. As the crude is poured in water (500 mL), precipitation occurs. The solid is filtered, washed with water and dried under vacuum overnight. The pale-brown solid obtained (23.4 g) is used in the next step without further purification.

Workup

  1. customprecipitation
  2. filtrationThe solid is filtered
  3. washwashed with water
  4. customdried under vacuum overnight
  5. customThe pale-brown solid obtained (23.4 g)
  6. customis used in the next step without further purification

Sources & evidence

ORD record
ord-61fba52e49364d828bdaf9989255217d
Source dataset
uspto-grants-2011_06
Patent number
US07968724B2

Reaction notes

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