Salicylaldehyde → HCID 19074348, compound

HRID 964934Notes

Reaction equation

HRID 964934 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br:10][C:11]1[CH:16]=[CH:15][C:14](F)=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1>CN(C=O)C>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1

Participants

4

Reactant 2

HCID 6998SalicylaldehydeHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 19074348HCID 19074348, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of 2-hydroxybenzaldehyde (16.7 g) and Al2O3 /KF (65.5 g) in DMF was heated to 120° C. under a N2 atmosphere and 4-bromo-1-fluoro-2-nitrobenzene (30 g) in DMF was added. The mixture was stirred at 120° C. for 3 hours. The precipitate was filtered off and the filtrate evaporated. The residue was purified by open column chromatography over silica gel (eluent 1: hexane/CH2Cl2 /AcOEt 8/1/1; eluent 2: CH2Cl2 /2-propanone 9/1) and the pure fractions were collected, yielding 26 g (59%) of 2-(4-bromo-2-nitrophenoxy)benzaldehyde (interm. 3). Analogously, 5-chloro-2-(2-nitrophenoxy)benzaldehyde (interm. 4) was prepared.

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe filtrate evaporated
  3. customThe residue was purified by open column chromatography over silica gel (eluent 1: hexane/CH2Cl2 /AcOEt 8/1/1; eluent 2: CH2Cl2 /2-propanone 9/1)
  4. customthe pure fractions were collected

Sources & evidence

ORD record
ord-99fff4d1adb442f8a7e328818b7b2cb9
Source dataset
uspto-grants-1998_06
Patent number
US05773433

Reaction notes

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