3-Hydroxybenzaldehyde → HCID 15186783, compound

HRID 2307659Notes

Reaction equation

HRID 2307659 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 15186783HCID 15186783, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-Hydroxybenzaldehyde (1.15 g, 9.4 mmol), 1-fluoro-4-nitrobenzene (1.0 mL, 9.4 mmol) and K2CO3 (2.61 g, 19 mmol) were combined in DMF (20 mL) and heated at 80° C. After 6 hours, the reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The separated aqueous phase was extracted with diethyl ether. The organic layers were combined, washed with 1N NaOH, brine, dried (MgSO4), filtered and the filtrate concentrated under reduced pressure to provide the title compound as a yellow solid (1.98 g).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. custompartitioned between water and diethyl ether
  3. extractionThe separated aqueous phase was extracted with diethyl ether
  4. washwashed with 1N NaOH, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-68e1d0d0ece44fcb9c2a6e287e360d78
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

Loading…