Diisopropylamine → HCID 22260708, compound

HRID 1983499Notes

Reaction equation

HRID 1983499 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[O:21][CH3:22].[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=[O:28].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[Br:13][C:14]1[C:15]([O:21][CH3:22])=[C:16]([CH:27]([C:26]2[CH:29]=[CH:30][CH:31]=[C:24]([F:23])[CH:25]=2)[OH:28])[C:17]([F:20])=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 680093-FluorobenzaldehydeHCID 70180432-Bromo-5-fluoroanisoleHCID 178418339Butyllithium

Product 1

HCID 22260708HCID 22260708, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

A total of 1.64 ml of diisopropylamine was dissolved in 27 ml of tetrahydrofuran, 6.8 ml of a 1.57 M solution of n-butyllithium in hexane was added at −50° C. under stirring, and the mixture was stirred at −30° C. for 30 minutes. After cooling to −60° C., 2 g of 1-bromo-4-fluoro-2-methoxy-benzene obtained in Production Example II-1-a was added and the mixture was stirred at −60° C. for 1 hour. Then, 1.55 ml of 3-fluoro-benzaldehyde was added, followed by stirring for 1 hour. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with diethyl ether. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated, to give 2.4 g of the title compound as a yellow-brown oil.

Workup

  1. stirringthe mixture was stirred at −30° C. for 30 minutes
  2. additionwas added
  3. stirringthe mixture was stirred at −60° C. for 1 hour
  4. stirringby stirring for 1 hour
  5. extractionthe mixture was extracted with diethyl ether
  6. washThe resulting organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9c12a42c2afc4beca3bc568c193d1f8c
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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