Ammonium Chloride → HCID 67458542, compound

HRID 554490Notes

Reaction equation

HRID 554490 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.[Br:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=[O:33])=[CH:30][CH:29]=1.[Cl-].[NH4+]>C1COCC1>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:32]([C:31]1[CH:34]=[CH:35][C:28]([Br:27])=[CH:29][CH:30]=1)[OH:33])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 707414-BromobenzaldehydeHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 178418244HCID 178418244, compound

Product 1

HCID 67458542HCID 67458542, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (1.59 M, 11.57 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (4.4 g, 16.72 mmol) in THF (168 mL) at −78° C. and the mixture solution was stirred at the same temperature for 15 minutes. To this solution, a solution of 4-bromobenzaldehyde (2.47 g, 13.34 mmol) in THF (50 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for 30 minutes and at 0° C. for 30 minutes, 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=ethyl acetate:n-hexane (1:10)] to obtain the title compound (4.08 g, 83%) as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 30 minutes and at 0° C. for 30 minutes
  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 (1:10)]

Sources & evidence

ORD record
ord-b9da60b1b4584fe8b3ff97773fa7dd9e
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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