Ammonium Chloride → (4-Bromonaphthalen-2-yl)-(5-methoxybenzo-[b]thiophen-2-yl)methanol

HRID 550245Notes

Reaction equation

HRID 550245 reaction equation
CCCCCC.C([Li])CCC.[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]2[S:18][CH:19]=[CH:20][C:16]=2[CH:15]=1.[Br:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]([CH:34]=[O:35])[CH:25]=1.[Cl-].[NH4+]>C1COCC1>[Br:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]([CH:34]([C:19]2[S:18][C:17]3[CH:21]=[CH:22][C:14]([O:13][CH3:12])=[CH:15][C:16]=3[CH:20]=2)[OH:35])[CH:25]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 36324255-Methoxy-1-benzothiopheneHCID 543381284-Bromonaphthalene-2-carbaldehydeHCID 178418244HCID 178418244, compound

Product 1

HCID 67157589(4-Bromonaphthalen-2-yl)-(5-methoxybenzo-[b]thiophen-2-yl)methanolYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (1.6 M, 1.48 ml, 2.36 mmol) was added dropwise to a solution of 5-methoxybenzo[b]thiophene (388 mg, 2.36 mmol) in THF (6 ml) at −78° C. and the reaction solution was stirred at the same temperature for 10 minutes. To this solution, a solution of 4-bromonaphthalene-2-carbaldehyde (530 mg, 2.25 mmol) in THF (4 ml) was added dropwise. The reaction mixture was stirred at the same temperature for two hours, and then a saturated ammonium chloride aqueous solution added 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 (725 mg, 77%).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for two 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=ethyl acetate:n-hexane (1:10)]

Sources & evidence

ORD record
ord-dfa510d4843b41ecb6227898c344d178
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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