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

HRID 550228Notes

Reaction equation

HRID 550228 reaction equation
C([SiH](CC)CC)C.[S:8]1[C:12]([CH:13]([C:15]2[CH:24]=[C:23]([Br:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)O)=[CH:11][C:10]2[CH:26]=[CH:27][CH:28]=[CH:29][C:9]1=2.CO.O>C(Cl)Cl>[Br:25][C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH2:13][C:12]2[S:8][C:9]3[CH:29]=[CH:28][CH:27]=[CH:26][C:10]=3[CH:11]=2)[CH:24]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 12052TriethylsilaneHCID 67156452(Benzo[b]thiophen-2-yl)-(4-bromo-naphthalen-2-yl)methanol

Product 1

HCID 671563652-(4-Bromonaphthalen-2-ylmethyl)-benzo[b]thiopheneYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, triethylsilane (0.48 ml, 3.01 mmol) and a boron trifluoride-diethyl ether complex (0.34 ml, 2.71 mmol) were added dropwise to a solution of (benzo[b]-thiophen-2-yl)-(4-bromonaphthalen-2-yl)methanol (1.0 g, 2.71 mmol) in methylene chloride (30 mL) at 0° C. The reaction mixture was stirred at room temperature for three hours, and then a 50% methanol aqueous solution (1 ml) was added and further water was added thereto 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 (1:40)] to obtain the title compound (0.82 g, 85.6%).

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 (1:40)]

Sources & evidence

ORD record
ord-f0fd9f556ab1475b8f1e26d1d0f90cfe
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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