Methanol → 2-(4-Bromonaphthalen-2-ylmethyl)-5-ethylbenzo[b]thiophene

HRID 550249Notes

Reaction equation

HRID 550249 reaction equation
C([SiH](CC)CC)C.[Br:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH:19]([C:21]2[S:25][C:24]3[CH:26]=[CH:27][C:28]([CH2:30][CH3:31])=[CH:29][C:23]=3[CH:22]=2)O)[CH:10]=1.CO.O>C(Cl)Cl>[Br:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH2:19][C:21]2[S:25][C:24]3[CH:26]=[CH:27][C:28]([CH2:30][CH3:31])=[CH:29][C:23]=3[CH:22]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 12052TriethylsilaneHCID 67156704(4-Bromo-naphthalen-2-yl)-(5-ethylbenzo[b]-thiophen-2-yl)methanol

Product 1

HCID 671572602-(4-Bromonaphthalen-2-ylmethyl)-5-ethylbenzo[b]thiopheneYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, triethylsilane (0.63 ml, 3.93 mmol) and a boron trifluoride-diethyl ether complex (0.27 ml, 2.16 mmol) were added to a solution of (4-bromo-naphthalen-2-yl)-(5-ethylbenzo[b]-thiophen-2-yl)methanol (780 mg, 1.96 mmol) in methylene chloride (20 ml) at 0° C. and the reaction mixture was stirred at room temperature for three hours. To the obtained solution was added methanol (10 ml) and water (30 ml) and the mixture was extracted with methylene chloride. 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)] to obtain the title compound (460 mg, 62%).

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. distillationthe solvent was distilled under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [

Sources & evidence

ORD record
ord-9f17f36f8de94293bc838e2b0eee9899
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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