Ammonium Chloride → HCID 67304191, compound

HRID 1009877Notes

Reaction equation

HRID 1009877 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=1.C([Li])CCC.[CH2:19]([O:26][C:27]1[C:34]([Br:35])=[CH:33][C:30]([CH:31]=[O:32])=[C:29]([Cl:36])[CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:19]([O:26][C:27]1[C:34]([Br:35])=[CH:33][C:30]([CH:31]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=2)[OH:32])=[C:29]([Cl:36])[CH:28]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 155094031-Bromo-4-[2-(methoxymethoxy)ethyl]benzeneHCID 866384434-(Benzyloxy)-5-bromo-2-chlorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 67304191HCID 67304191, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a tetrahydrofuran solution (6 mL) of 1-bromo-4-[2-(methoxymethoxy)ethyl]benzene (1.52 g, 6.20 mmol) was added dropwise under nitrogen atmosphere at −78° C. a 2.6 M hexane solution of n-butyllithium (2.38 mL, 6.20 mmol), and the mixture was stirred for 10 minutes at the same temperature. Then a tetrahydrofuran solution (6 mL) of 4-(benzyloxy)-5-bromo-2-chlorobenzaldehyde (2.02 g, 6.20 mmol) was added dropwise over 10 minutes, and the mixture was stirred for 30 minutes at the same temperature. To the reaction solution was added a saturated aqueous solution of ammonium chloride, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride and brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain the title compound (750 mg, 25%) as a colorless oily compound.

Workup

  1. stirringthe mixture was stirred for 30 minutes at the same temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure
  7. customThus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-7768ddf5099e45f6bc64afeaa07fb1e4
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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