Ammonium Chloride → HCID 67459722, compound

HRID 554549Notes

Reaction equation

HRID 554549 reaction equation
CCCCCC.C([Li])CCC.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH:31]=[O:32].[Cl-].[NH4+]>C1COCC1>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:31]([C:30]1[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:28]([F:27])[CH:29]=1)[OH:32])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 676963-Fluoro-p-anisaldehydeHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 178418244HCID 178418244, compound

Product 1

HCID 67459722HCID 67459722, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (1.54 M, 6.79 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (2.5 g, 9.50 mmol) in THF (30 mL) at −78° C. and the mixture was stirred at the same temperature for 30 minutes. To this solution, a solution of 3-fluoro-4-methoxybenzaldehyde (1.32 g, 8.56 mmol) in THF (8 mL) was added dropwise at −78° C. The mixture was stirred at the same temperature for one hour, and then a saturated ammonium chloride aqueous solution was added thereto and the mixture was extracted with ethyl acetate, and 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=ethyl acetate:n-hexane (1:5)] to obtain the title compound (2.79 g, 96%).

Workup

  1. stirringThe mixture was stirred at the same temperature for one hour
  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=ethyl acetate:n-hexane (1:5)]

Sources & evidence

ORD record
ord-bc048388697f42b1aeb410986467dbda
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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