2-Naphthalenecarboxaldehyde → HCID 22260898, compound

HRID 1983516Notes

Reaction equation

HRID 1983516 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[O:21][CH3:22].[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[CH:33]=[O:34]>CCCCCC.O1CCCC1.O>[Br:13][C:14]1[C:15]([O:21][CH3:22])=[C:16]([CH:33]([C:24]2[CH:25]=[CH:26][C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:23]=2)[OH:34])[C:17]([F:20])=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 62012-NaphthalenecarboxaldehydeHCID 7912DiisopropylamineHCID 70180432-Bromo-5-fluoroanisoleHCID 178418339Butyllithium

Product 1

HCID 22260898HCID 22260898, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In an atmosphere of nitrogen gas, 2.38 ml of a 2.66 M solution of n-butyllithium in hexane was added to a solution of 0.64 g of N,N-diisopropylamine in 9 ml tetrahydrofuran at −78° C. After stirring at the same temperature for 1 hour, 1.18 g of 1-bromo-4-fluoro-2-methoxy-benzene obtained in Production Example II-1-a was added dropwise. After stirring at the same temperature for 1 hour and 20 minutes, a solution of 0.99 g of 2-naphthoaldehyde in 4 ml tetrahydrofuran was added dropwise. After stirring at the same temperature for 1 hour and 20 minutes, water was added under ice-cooling and the mixture was extracted with diethyl ether for two times. The extract was sequentially washing with water and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography, to give 1.72 g of the title compound as a pale yellow oil.

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring at the same temperature for 1 hour and 20 minutes
  3. stirringAfter stirring at the same temperature for 1 hour and 20 minutes
  4. temperaturecooling
  5. extractionthe mixture was extracted with diethyl ether for two times
  6. washThe extract was sequentially washing with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe crude product was purified
  10. customseparated by silica gel column chromatography

Sources & evidence

ORD record
ord-4cb680139d3b441f8c95642e62dff52a
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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