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[ CAS No. 10133-20-7 ] {[proInfo.proName]}

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Chemical Structure| 10133-20-7
Chemical Structure| 10133-20-7
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Product Details of [ 10133-20-7 ]

CAS No. :10133-20-7 MDL No. :
Formula : C9H7BrS Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 227.12 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 10133-20-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 10133-20-7 ]

[ 10133-20-7 ] Synthesis Path-Downstream   1~9

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  • [ 24155-42-8 ]
  • [ 99592-23-1 ]
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  • [ 17890-56-1 ]
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YieldReaction ConditionsOperation in experiment
100% With hydrogen bromide; acetic acid; In dichloromethane; at 20℃; for 3h; Step 1: 2-(Bromomethyl)benzo[b]thiopheneHBr in acetic acid (6 mL) was added to a suspension of benzo[b]thiophen-2- ylmethanol (1 g, 6.1 mmol) in dichloromethane (6 mL) at room temperature. The reaction mixture was stirred for 3 hours then diluted by addition of chloroform (20 mL). The organic phase was washed with a saturated solution of hydrogenocarbonate (20 mL), dried over sodium sulfate and concentrated to dryness. The title product was obtained as a yellow oil (1.3 g, quantitative).*H NMR (CDCI3, 400 MHz) : delta (ppm) : 7.91 (m, 1H), 7.83 (m, 1H), 7.53-7.45 (m, 2H), 7.33 (s, 1 H), 4.86 (s, 2H).
97% With hydrogen bromide; In dichloromethane; REFERENCE EXAMPLE 6 Benzothiophen-2-methylbromide The alcohol prepared in Reference Example 5 (821 mg, 5 mmol) was dissolved in dichloromethane (5 mL). To the solution was added 47percent hydrobromic acid (5 mL) and the mixture was stirred at room temperature for 4 hours. The reaction was diluted with chloroform (50 mL), and the solution was washed with 5percent aqueous sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under a reduced pressure to give the title compound (1.1 g, 97percent) as a pale yellow solid. 1H-NMR (CDCl3, 270 MHz) delta=7.83-7.66 (m, 2H), 7.37-7.24 (m, 3H), 4.77 (s, 2H).
With phosphorus tribromide; In diethyl ether; at 20℃; for 1h; General procedure: To a solution of the alcohol 12b (1.55 g; 7.59 mmol) in diethyl ether (12 mL) was added phosphorous tribromide (0.36 mL; 11.4 mmol) dropwise at ambient temperature. The reaction was stirred at ambient temperature for 1h, diluted with EtOAc, washed with aqueous NaHCO3, H2O, brine, dried over Na2SO4, filtered and the solvent evaporated under reduced pressure to afford the methylene bromide (not shown). To a solution of the methylene bromide in toluene (20 mL) was added triethyl phosphate (3.78 mL; 22.8 mmol), and the reaction was refluxed for 18h. The reaction mixture was cooled, concentrated under reduced pressure and the resultant residue was purified by flash column chromatography (silica gel), eluting with a hexanes-ethyl acetate gradient to afford 1.85 g (75percent) of phosphonate (not shown) as an oil. To a solution of the phosphonate (0.094 g; 0.291 mmol) in THF (2.0 mL) cooled to -70 °C, was added a 2.5 M solution of n-butyllithium in hexanes (0.175 mL; 0.437 mmol), dropwise. The reaction mixture was allowed to stir at -70 °C for 30 min, to which was then added a solution of 3,4-difluorobenzyl bromide (0.09 g; 0.435 mmol) in THF (1.0 mL), dropwise. The reaction mixture was allowed to slowly warm to ambient temperature, and stirred for an additional 30 min before quenching with a solution of saturated aqueous NH4Cl (1.0 mL). The mixture was diluted with EtOAc, washed with H2O, brine, dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by reverse-phase semi-prep HPLC eluting with a 55percent MeCN-H2O (0.1percent TFA) to 75percent MeCN-H2O (0.1percent TFA) gradient to afford 0.048 g (37percent) of compound 13b as an oil
With phosphorus tribromide; In dichloromethane; at 0℃; for 0.5h;Inert atmosphere; General procedure: To a suspension of LiAlH4 (4.60 g,121.2 mmol) in dry THF (150 mL) at 0 oC, methylbenzo[b]thiophene-2-carboxylate 14 (10 g, 48.5 mmol) indry THF (30 mL) was slowly added via syringe. After the addition of the compound, the reaction mixture was stirred at 0 °C for 30 min. Then, it was quenched with methanol (5 drops), followed by 5 percent NaOH (6 mL). The insoluble residue was filtered off and dried (Na2SO4). The removal of the solvent in vacuo afforded crude alcohol. The solution of crude benzo[b]thiophene-2-methanol (6.5 g, 39.5 mmol) in dry DCM (80 mL) at 0 oC,PBr3 (7.5 mL, 79.1 mmol) was added slowly through syringe and the reaction mixture was then stirred at room temperature for 30 min under N2 atmosphere. After the reaction was completed (monitored by TLC), it was diluted with ice water and the organic layer was extracted with DCM (2 x 50 mL) and dried (Na2SO4).Removal of solvent in vacuo afforded bromomethyl benzo[b]thiophene as a colorless solid. The bromocompound (9.0 g, 32.4 mmol) was reacted with triethyl phosphite (16.5 mL, 97.2 mmol) at reflux under N2 for2 h. After consumption of the bromo compound (monitored by TLC), the reaction mass was poured over crushed ice (100 g) containing Conc. HCl (2 mL) and extracted with DCM (3x50 mL). The organic layer was washed with brine (2 x 50 mL) and dried (Na2SO4). The solvent was removed under vacuo to give crude phosphonate ester 15 as a thick brown liquid. The crude product was used as such for next step without any further purification. Yield: 10.1 g (67percent) over 3 steps.

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  • [ 15862-72-3 ]
  • [ 181580-88-1 ]
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  • [ 144978-12-1 ]
  • [ 400626-22-4 ]
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  • [ 10133-20-7 ]
  • [ 18711-13-2 ]
  • 1-benzo[<i>b</i>]thiophen-2-ylmethyl-4,7-dichloro-1<i>H</i>-indole-2,3-dione [ No CAS ]
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  • [ 10133-20-7 ]
  • [ 112656-95-8 ]
  • 1-benzo[<i>b</i>]thiophen-2-ylmethyl-7-nitro-1<i>H</i>-indole-2,3-dione [ No CAS ]
  • 9
  • [ 10133-20-7 ]
  • [ 123770-62-7 ]
  • ethyl 5-(benzothiophen-2-ylmethoxymethyl)isoxazole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1 g Reference Production Example 91 (0733) 60% Sodium hydride (1.04 g, 26.3 mmol) was added to dehydrated N,N-dimethylformamide (10 ml) cooled to 0C, under a nitrogen atmosphere, and a dehydrated N,N-dimethylformamide (10 ml) solution of <strong>[123770-62-7]ethyl 5-hydroxymethylisoxazole-3-carboxylate</strong> (3.0 g, 17.54 mmol) was added dropwise thereto, and then the mixture was further stirred for 30 minutes. A dehydrated N,N-dimethylformamide (5 ml) solution of 2-bromomethylbenzothiophene (4.0 g, 17.54 mmol) was added thereto, and the mixture was heated to room temperature and stirred for 16 hours. Then, the mixture was added to a saturated aqueous ammonium chloride solution, and extracted twice with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 1.0 g of ethyl 5-(benzothiophen-2-ylmethoxymethyl)isoxazole-3-carboxylate represented by the following formula. 1H-NMR (CDCl3, TMS, delta(ppm)):7.82(d, 1H), 7.75(d, 1H), 7.34-7.31(m, 2H), 7.20(m, 1H), 6.70(s, 1H), 4.90(s, 2H), 4.70(s, 2H), 4.45(q, 2H), 1.40(s, 3H)
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