Triethylsilane → 2-(4-Bromonaphthalen-2-ylmethyl)-5-fluorobenzo[b]thiophene

HRID 550235Notes

Reaction equation

HRID 550235 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]([F:30])=[CH:29][C:23]=3[CH:22]=2)O)[CH:10]=1.C(=O)([O-])O.[Na+]>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]([F:30])=[CH:29][C:23]=3[CH:22]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 67156712(4-Bromo-naphthalen-2-yl)-(5-fluorobenzo[b]-thiophen-2-yl)methanol

Product 1

HCID 671565772-(4-Bromonaphthalen-2-ylmethyl)-5-fluorobenzo[b]thiopheneYield 215.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, triethylsilane (0.18 ml, 2.11 mmol) and a boron trifluoride-diethyl ether complex (0.25 ml, 1.94 mmol) were added to a solution of (4-bromo-naphthalen-2-yl)-(5-fluorobenzo[b]-thiophen-2-yl)methanol (260 mg, 0.65 mmol) in methylene chloride (10 ml) at 0° C. and the mixture was stirred a room temperature for two hours. A saturated sodium hydrogen carbonate aqueous solution was added 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=ethyl acetate:n-hexane (1:100)] to obtain the title compound (520 mg, 80%).

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 [developing solution=ethyl acetate:n-hexane (1:100)]

Sources & evidence

ORD record
ord-6e649d73c71c447597e84b19ea0769e8
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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