Benzo(B)Thiophene → Benzo[b]thiophen-2-yl-(4-bromo-1-methoxynaphthalen-2-yl)methanol

HRID 550240Notes

Reaction equation

HRID 550240 reaction equation
CCCCCC.C([Li])CCC.[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[CH:13]1.[Br:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([O:32][CH3:33])=[C:24]([CH:34]=[O:35])[CH:23]=1.[Cl-].[NH4+]>C1COCC1>[S:12]1[C:13]([CH:34]([C:24]2[CH:23]=[C:22]([Br:21])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]=2[O:32][CH3:33])[OH:35])=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2

Participants

6

Reactant 4

HCID 7221Benzo(B)ThiopheneHCID 25517Ammonium ChlorideHCID 862219444-bromo-1-methoxy-2-NaphthalenecarboxaldehydeHCID 178418244HCID 178418244, compound

Product 1

HCID 67156311Benzo[b]thiophen-2-yl-(4-bromo-1-methoxynaphthalen-2-yl)methanolYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (1.6 M, 6.2 ml, 9.90 mmol) was added dropwise to a solution of benzothiophene (1.33 g, 9.90 mmol) in THF (20 ml) at −78° C. and the reaction mixture was stirred at the same temperature for 10 minutes. To this mixture, a solution of 4-bromo-1-methoxynaphthalene-2-carbaldehyde (2.5 g, 9.43 mmol) in THF (30 ml) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for two hours, and then a saturated ammonium chloride aqueous solution was added thereto and the mixture was extracted with ether. 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 (1:4)] to obtain the title compound (3.12 g, 83%).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for two hours
  2. extractionthe mixture was extracted with ether
  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 (1:4)]

Sources & evidence

ORD record
ord-1032e3f441284d5f818610872a48d73d
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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