Alternatived Products of [ 741290-20-0 ]
Product Details of [ 741290-20-0 ]
| CAS No. : | 741290-20-0 |
MDL No. : | MFCD18413278 |
| Formula : |
C9H5F3O
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
186.13
|
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 741290-20-0 ]
Application In Synthesis of [ 741290-20-0 ]
* 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 [ 741290-20-0 ]
- 1
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[ 741290-08-4 ]
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[ 741290-20-0 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With PPA; In benzene; at 90℃; for 6h; |
To a round-bottom flask containing 1- (2, 2-diethoxy-ethoxy) -4-trifluoromethylbenzene (8.25 g, 29.6 mmol, 1 eq) and benzene (80 mL, anhydrous) was added polyphosphoric acid (8.2 g). The mixture was HEATED TO 90 C for 6 hours. The solvent was removed carefully in vacuo and the crude mixture was applied to A silica gel column. Elution with n-hexanes gave pure fractions of product which were carefully concentrated to give 1.32 G OF A COLOURLESS,. oily mixture of title compound and n-hexanes (suspected volatility of title compound), which was used without futher purification. |
|
With polyphosphoric acid; In benzene; for 2.5h;Reflux; |
-(Trifluoromethyl)- 1 -benzofuranTo a mixture of benzene (100 mL) containing polyphosphoric acid (19.45 g, 57.54 mmol) was added l-(2,2-diethoxyethoxy)-4-(trifluoromethyl)benzene (8.0 g, 28.75 mmol). The mixture was stirred vigorously while being heated to reflux for 2.5 hours. The reaction mixture was cooled to room temperature and decanted from the polyphosphoric acid. The solvent was removed under vacuum to give the residue, which was purified by silica gel column chromatography eluting with 1 % ethyl acetate in petroleum ether to afford 5- (trifluoromethyl)-l -benzofuran (5.0 g, crude) as colorless oil. 'H-NMR (300 MHz, CDCI3): delta 7.93 (s, 1H), 7.75 (d, J = 2.4 Hz, 1H), 7.56 - 7.64 (m, 2H), 6.87 - 6.88 (m, 1H) |
- 2
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[ 741290-20-0 ]
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[ 68-12-2 ]
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[ 496949-41-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|
|
A round-bottom flask under argon was charged with the above mixture of 5- trifluoromethylbenzofuran and n-hexanes (1.32 g). THF (130 mL, anhydrous) was added and the flask was cooled TO-78 C. A solution of n-butyllithium in n-hexanes (6.88 mL of a 1.6 M solution) was added. After stirring for 5 min. , the mixture, N, N-DIMETHYLFORMAMIDE (27 mL) was added dropwise. Stirring continued for 2 hours AT-78 C. The mixture was quenched through slow addition of a saturated solution of NH4C1 and submitted to extractive workup with diethyl ether. The combined organics were dried on MGS04, filtered and concentrated in vacuo to give a crude residue (1.51 g) which was used immediately, without purification, in the subsequent protocol. |
- 3
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[ 402-45-9 ]
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[ 741290-20-0 ]
- 4
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[ 741290-20-0 ]
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[ 1396752-78-5 ]
- 5
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[ 741290-20-0 ]
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[ 5419-55-6 ]
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[ 7732-18-5 ]
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[ 1396752-77-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|
|
-(Trifluoromethyl)-l-benzofuran-2-yl]boronic acidTo a solution of 5-(trifluoromethyl)-l-benzofuran (5.0 g, 26.86 mmol) in dry tetrahydrofuran (120 mL) were added tetramethylethylenediamine (3.74 g, 32.2 mmol). The solution was kept below -60C. under nitrogen, while n-BuLi (12.8 mL, 32.2 mmol, 2.5 M solution in hexane) was added dropwise. The solution was warmed to -10C over 45 min and stirred at this temperature for another 30 min. The mixture was cooled again below -60C followed by dropwise addition of triisopropyl borate (10.0 g, 53.19 mmol). After warming to room temperature the mixture was quenched with hydrochloric acid (70 mL, 2N) and stirred for 1 h. The alkaline aqueous layer was brought to pH 5 and extracted with ethyl acetate (3 x 80 mL). All organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give [5-(trifluoromethyl)-l-benzofuran-2-yl]boronic acid (2.0 g, crude) as light yellow oil; which was used for the next step without further purification. |
- 6
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[ 741290-20-0 ]
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[ 95-92-1 ]
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C13H9F3O4
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 47% |
|
[000427] To a solution of Compound 30C (690 mg, 3.71 mmol) in petroleum ether from last step and anhydrous THF (10 mL) was added n-BuLi (2.5 M in hexane, 1.78 mL) at -78 C under N2. After stirred for 30 min, to the mixture was added diethyl oxalate (2.7 g, 18.5 mmol). Stirred at -78 C for 1 h, it was quenched with sat. aq NH4C1, and extracted with ethyl acetate (50 mL x 2). The combined extracts were washed with brine (50 mL x 1), dried over Na2S04i concentrated and recrystallized from MeOH (3 mL) to afford Compound 30D (500 g, yield 47%) as a yellow solid. 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 1.35-1.38 (t, J= 7.2 Hz, 3H), 4.37-4.43 (q, J= 7.6 Hz, 2H), 7.93-8.03 (m, 2H), 8.34 (s, 1H), 8.42-8.44 (m, 1H). |
- 7
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1-(2,2-dimethoxyethoxy)-4-(trifluoromethyl)benzene
[ No CAS ]
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[ 741290-20-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 19% |
With polyphosphoric acid; In toluene; at 80℃; for 2h; |
[000426] A solution of polyphosphoric acid (8.1 g, 24 mmol) in toluene (10 mL) was added compound 30B (5 g, 20 mmol) in toluene (10 mL) and the mixture was stirred at 80 C for 2 h. It was then poured into ice, stirred for 30 min, and extracted with DCM (50 mL x 3). The combined extracts were washed with brine (50 mL x 1), dried over Na2S04, concentrated, and purified by column chromatography on silica gel (petroleum, 100%) v/v) to afford Compound 30C (690 mg, yield 19%) as a yellow solution in petroleum. 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 6.79 (s, 1H), 7.54 (m, 2H), 7.67 (s, 1H), 7.87 (s, 1H). |
- 8
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[ 741290-20-0 ]
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C13H9F5O3
[ No CAS ]
- 9
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[ 741290-20-0 ]
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C11H5F5O3
[ No CAS ]
- 10
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[ 741290-20-0 ]
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N-((1R,2R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)-2,2-difluoro-2-(5-(trifluoromethyl)benzofuran-2-yl)acetamide
[ No CAS ]
- 11
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[ 741290-20-0 ]
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[ 106-43-4 ]
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C16H11F3O
[ No CAS ]
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