Ammonium Chloride → HCID 67461295, compound

HRID 554525Notes

Reaction equation

HRID 554525 reaction equation
CCCCCC.C([Li])CCC.[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1.[Cl-].[NH4+]>C1COCC1>[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[CH:34]([C:33]1[CH:36]=[CH:37][C:30]([O:29][CH3:28])=[CH:31][CH:32]=1)[OH:35])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 312444-MethoxybenzaldehydeHCID 192614712-(Benzyloxy)-1-bromo-4-fluorobenzeneHCID 178418244HCID 178418244, compound

Product 1

HCID 67461295HCID 67461295, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (1.59 M, 3.14 mL) was added dropwise to a solution of 2-benzyloxy-1-bromo-4-fluorobenzene (1.4 g, 5.0 mmol) in THF (50 ml) at −78° C. and the mixture was stirred at the same temperature for 15 minutes. To this solution, a solution of 4-methoxybenzaldehyde (680 mg, 4.99 mmol) in THF (15 mL) was added dropwise at −78° C. and the mixture was stirred at the same temperature for 1.5 hours, and then a saturated ammonium chloride aqueous solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=n-hexane:dichloro-methane:acetone (12:3:1)] to obtain the title compound (1.41 g, 83%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1.5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. distillationthe solvent was distilled under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [developing solution=n-hexane:dichloro-methane:acetone (12:3:1)]

Sources & evidence

ORD record
ord-816c656fa59c4c069bb1f23e3b4fbb39
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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