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Methanol → 2-(4-Bromo-1-methoxynaphthalen-2-yl-methyl)benzo[b]thiophene

HRID 550241
Notes
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Reaction equation

HRID 550241 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)[C:16]=2[O:26][CH3:27])O)=[CH:11][C:10]2[CH:28]=[CH:29][CH:30]=[CH:31][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)[C:16]([O:26][CH3:27])=[C:15]([CH2:13][C:12]2[S:8][C:9]3[CH:31]=[CH:30][CH:29]=[CH:28][C:10]=3[CH:11]=2)[CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 12052TriethylsilaneHCID 67156311Benzo[b]thiophen-2-yl-(4-bromo-1-methoxynaphthalen-2-yl)methanol

Product 1

HCID 666081932-(4-Bromo-1-methoxynaphthalen-2-yl-methyl)benzo[b]thiopheneYield 80%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

In a nitrogen stream, triethylsilane (2.48 ml, 15.5 mmol) and a boron trifluoride-diethyl ether complex (1.08 ml, 8.54 mmol) were added dropwise to a solution of benzo[b]thiophen-2-yl-(4-bromo-1-methoxynaphthalen-2-yl)methanol (3.1 g, 7.76 mmol) in methylene chloride (60 ml) at 0° C. and the reaction mixture was stirred at room temperature for two hours, and then a 50% methanol aqueous solution (1 ml) was added and furthermore water (30 ml) was added thereto. The resulting mixture was extracted with methylene chloride, and 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 (1:50)] to obtain the title compound (2.38 g, 80%).

Workup

  1. extractionThe resulting 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 (1:50)]

Sources & evidence

ORD record
ord-eb65cff3a7e047a2abf5ebc044186c82
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07943748B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes