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[ CAS No. 20532-30-3 ]

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2D
Chemical Structure| 20532-30-3
Chemical Structure| 20532-30-3
Structure of 20532-30-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 20532-30-3 ]

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Related Doc. of [ 20532-30-3 ]

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Product Details of [ 20532-30-3 ]

CAS No. :20532-30-3MDL No. :MFCD01860057
Formula :C9H8OSBoiling Point :268.874°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :164.22Pubchem ID :3632425
Synonyms :

Computed Properties of [ 20532-30-3 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 20532-30-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20532-30-3 ]

  • Downstream synthetic route of [ 20532-30-3 ]

[ 20532-30-3 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 72002-19-8 ]
  • [ 20532-30-3 ]
  • 2
  • [ 20532-30-3 ]
  • [ 79099-07-3 ]
  • 4-hydroxy-4-(5-methoxy-benzo[<i>b</i>]thiophen-2-yl)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 4
  • [ 91906-21-7 ]
  • [ 20532-30-3 ]
YieldReaction ConditionsOperation in experiment
75% With Amberlyst-15; In chlorobenzene; at 120℃; for 3h; General procedure: To a solution of 13a (or 13b) (3 mmol) in 30 mL of chlorobenzene was added Amberlyst-15 (10 wt%). The mixture was heated at 120C for 3h. After cooling down to room temperature, the mixture was filtered and the solvent was removed under reduced pressure. The residue were purified on silica gel (EP/Et2O 8/2) to give compound 14a (or 14b) as yellow oil with 78% (or 75%) yield. 1H and 13C spectra of compounds 14a-b were in agreement with literature data.
47% With PPA; In chlorobenzene; at 135℃; for 1.5h; Step B: A solution of the product from Step A (15.0 g, 58.5 mmol) in chlorobenzene (65 ml) was added dropwise to a solution of polyphosphoric acid (125 g) in chlorobenzene (375 ml) heated to 135 C. After stirring at 135 C. for 1.5 hours, the mixture was cooled below 50 C. The chlorobenzene layer was poured out of the reaction flask and was concentrated under vacuum. Meanwhile, water was added to the reaction vessel to decompose polyphosphoric acid. The resulting aqueous phase was added to the residue from the chlorobenzene layer. Additional water and dichloromethane were added and the two phases were separated. The aqueous layer was extracted with dichloromethane twice. The combined organic extracts were dried with sodium sulfate and concentrated under vacuum. The crude material was purified by chromatography (15:1 heptane/ethyl acetate) to give the cyclized product (4.5 g, 47%, 100% AUC GC): 1H NMR (300 MHz, CDCl3) delta 7.87 (d, J=9.0 Hz, 1H), 7.58 (d, J=5.4 Hz, 1H), 7.39-7.42 (m, 2H), 7.14 (dd, J=9.0, 2.4 Hz, 1H), 4.01 (s, 3H).
  • 5
  • [ 20532-30-3 ]
  • [ 19301-35-0 ]
YieldReaction ConditionsOperation in experiment
81% With boron tribromide-dimethyl sulfide complex; In dichloromethane; chlorobenzene; at 0 - 120℃;Inert atmosphere; General procedure: To a solution of 14a (or 14b) (2 mmol) in anhydrous chlorobenzene (20 mL) a solution of BBr3SMe2 1M in CH2Cl2 (4 mL, 4 mmol) was added dropwise at 0C and under Ar atmosphere. The reaction was kept stirring at reflux for 10h. After cooling down, the reaction was quenched with water and extracted with CH2Cl2 (three times). The organic layers were collected, dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The crude was purified on silica gel to afford compounds 9a (or 9b) with 80% (or 81%) yield. 1H and 13C spectra of compounds 9a-b were in agreement with literature data.[1]
73% With boron tribromide; In dichloromethane; at -10 - 20℃; for 1.5h;Inert atmosphere; To a solution of Example 20a (1.5 g, 9.14 mmol, 1.0 eq) in DCM (20 mL) was added dropwise BBr3 (36.6 ml, 36.6 mmol, 4.0 eq, 1M in DCM) at -10C under N2. The mixture was stirred at this temperature for 30 min, and then warmed to r.t. for 1 h. The reaction was quenched with MeOH at - 5C. The mixture was extracted with DCM (50 mL) and water. The organic layer was washed with aq.NaHC03, dried over Na2S04 and concentrated. The residue was purified by flash column chromatography (PE:EA=4: 1) to give the desired product(Example 20b, 1 g, yield 73%, as a yellow solid). MS [M+1]+=151.0
With pyridine hydrochloride; at 190℃; for 3.5h;Sealed tube; METHOD B. 5-HYDROXY-1-BENZOTHIOPHENE5-methoxy-1-benzothiophene (6.37 g, 38.8 mmol) was combined with pyridine hydrochloride (13.5 g, 116.4 mmol) in a sealed tube and heated to 190 C. for 3.5 hrs. The reaction was cooled to room temperature and the resulting residue was dissolved in 2:1 EtOAc-H2O with sonication. The organic layer was washed with water, brine, dried over anhydrous Na2SO4, and filtered. The filtrate was evaporated in vacuo. The crude residue was purified by silica gel chromatography using 20% EtOAc-hexanes to give 5-hydroxy-1-benzothiophene.1H NMR (500 MHz, acetone-d6) delta (ppm): 8.32 (s, 1H), 7.43 (d, J=8.8 Hz, 1H), 7.56 (d, J=5.5 Hz, 1H), 7.28 (d, J=2.3 Hz, 1H), 7.25 (d, J=5.3 Hz, 1H), 6.96 (dd, J=2.3 Hz, 1H).
Step 1. A 5.0 mL reaction vial was charged with 5-methoxy-l- benzothiophene (0.64 g, 3.9 mmol, Small Molecules, Hoboken, NJ) and pyridine hydrochloride (1.3 g, 12 mmol, Acros, Waltham, MA), and then the reaction mixture was heated at 190 C for 3.5 h. After that time, the reaction mixture was cooled to room temperature, partitioned between ethyl acetate (100 mL) water (50 mL), the layers were separated, the organic material was washed with brine (25 mL), dried (magnesium sulfate), filtered, and the filtrate was concentrated. The isolated material (0.64 g) was used in the next step of the synthesis without purification.
With pyridine hydrochloride; at 190℃; for 3.5h;Sealed tube; Neat (no solvent); PREPARATIVE EXAMPLE 23 GENERAL PREPARATION OF BENZOTHI OPHENESMETHOD A. 5-HYDROXY-l -BENZOTHIOPHENE5-Methoxy-l -benzothiophene (6.37 g, 38.8 mmol) was combined with pyridine hydrochloride (13.5 g5 1 16.4 mmol) in a sealed tube and heated to 19O0C for 3.5 hrs. The reaction was cooled to room temperature and the resulting residue was dissolved in 2:1 EtOAc-H2O with sonication. The organic layer was washed with water, brine, dried over anhydrous Na2SO4, and filtered. The filtrate was evaporated in vacuo. The crude residue was purified by silica gel chromatography using 20% EtOAc-hexanes to give 5-hydroxy-l -benzothiophene.1H NMR (500 MHz, acetone-d6) deltappm): 8.32 (s, IH), 7.43 (d, J=8.8 Hz, IH), 7.56 (d, J=5.5 Hz, IH), 7.28 :d, J=2.3 Hz, IH), 7.25 (d, J=5.3 Hz5 IH); 6.96 (dd, J=2.3 Hz5 I H).

  • 6
  • [ 19301-35-0 ]
  • [ 77-78-1 ]
  • [ 20532-30-3 ]
YieldReaction ConditionsOperation in experiment
24% With polyphosphoric acid; In chlorobenzene; at 130℃; for 4h;Inert atmosphere; General procedure: Polyphosphoric acid (PPA, 15g, 0.044mol) and chlorobenzene (30 mL) were mixed in three flasks purged with argon three times and heated to 130C , plus, Dissolved in chlorobenzene (10 mL) of (2,2-diethoxyethyl)(4-fluorophenyl)sulfane (Formula B4,3.6g, 0.015mol), stirred for 4 hours, cooled. Cooling to room temperature, water (100ml), extracted with petroleum ether three times (50ml), washed once with saturated brine (50ml), dried over sodium sulfate, silica gel columnChromatography, eluted with petroleum ether to give an orange-red liquid (formula B5,0.75g, 33%).
  • 8
  • [ 20532-30-3 ]
  • 5-methoxy-2-(methylsulfinyl)benzothiophene [ No CAS ]
Reference: [1]Tetrahedron,2020
  • 9
  • [ 20532-30-3 ]
  • 4-methoxy-N-(2-(5-methoxy-2-(methylsulfanyl)benzothiophen-3-yl)-4-methylphenyl)benzenesulfonamide [ No CAS ]
Reference: [1]Tetrahedron,2020
  • 10
  • [ 20532-30-3 ]
  • [ 624-92-0 ]
  • C10H10OS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: The synthesis of 7-methoxy-2-(methylsulfinyl)benzothiopheneis representative. A 50-mL round-bottom flask was charged with 7-methoxybenzothiophene (0.80 g, 4.9 mmol, prepared according to the literature [24]) and THF (10 mL). A solution of BuLi (1.6 M in hexane, 3.4 mL, 5.4 mmol) was added dropwise at 0 C. The resulting solution was stirred at 0 C for 1 h before an addition of dimethyl disulfide (0.45 mL, 5.1 mmol). After the mixture wasstirred for 1 h additionally, saturated aqueous NaHCO3 was added. The resulting biphasic solution was extracted with EtOAc(10 mL 3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to provide 7-methoxy-2-(methylsulfanyl)benzothiophene with some impurities. Subsequent oxidation of the sulfide according to GP1provided 7-methoxy-2-(methylsulfinyl)benzothiophene (0.89 g, 3.9 mmol, 80% over two steps) as a brown oil.
Reference: [1]Tetrahedron,2020
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