Structure of 109179-31-9
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CAS No. : | 109179-31-9 |
Formula : | C8H7BrO |
M.W : | 199.05 |
SMILES Code : | O=CC1=CC=CC(C)=C1Br |
MDL No. : | MFCD18392002 |
Boiling Point : | No data available |
InChI Key : | CYQUDJGXCABLPN-UHFFFAOYSA-N |
Pubchem ID : | 13707076 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<Step 2>NaH (60percent assay, 193 mg, 4.82 mmol) was suspended in DMF (10 mL) and then cooled to 0° C. Triethyl 2-phosphonopropionate (1.05 mg, 4.82 mmol) in DMF (10 mL) was added dropwise in a slow manner to the solution and then stirred for 15 minutes. Then, the aldehyde obtained from Step 1 (640 mg, 3.22 mmol) in DMF (3 mL) was added thereto in a slow manner and then stirred for 18 hours while gradually heating it from 0° C. to room temperature. EtOAc was then added to the reaction solution, washed with water and saturated saline and then dried over anhydrous MgSO4. The solvent was eliminated in vacuo to obtain a residue. The resulting residue was then dissolved in THF (10 mL) and MeOH (4 mL), 2 N NaOH (8 mL, 8 mmol) was added thereto and then stirred at room temperature for 8 hours. The solvent was then eliminated in vacuo, 2 N HCl was added to acidify the solution and then the crystals precipitated were filtrated to obtain white crystals of the objective carboxylic acid (600 mg, 93percent).MS: 256 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With pyridinium chlorochromate; In dichloromethane; at 20℃; | A solution of the (2-bromo-3-methylphenyl)methanol 35 (100mg, 0.49mmol, 1equiv), PCC (161mg, 0.75mmol, 1.5equiv), and Celite (0.48mg) in anhydrous CH2Cl2 (4.5mL) was stirred at room temperature overnight. The mixture was quenched by addition of brine and extracted with Et2O. Combined organic layers were washed with water, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Crude product was passed through a silica/Celite plug and concentrated to give 36 (94mg, 95percent) as a white solid. Rf=0.57 (Pentane/Et2O 95:5). 1H NMR (400MHz, CDCl3) delta (ppm)=10.45 (d, 4J=0.8Hz, 1H, H-8), 7.75?7.73 (m, 1H, H-6), 7.48 (ddd, 3J=7.6Hz, 4J=1.6Hz, 5J=0.8Hz, 1H, H-4), 7.32 (br t, 3J=7.6Hz, 1H, H-5), 2.48 (s, 3H, H-7). 13C NMR (125MHz, CDCl3) delta (ppm)=192.8 (C-8), 139.7 (C-3), 136.4 (C-4), 134.1 (C-1), 129.7 (C-2), 127.52 (C-5 or 6), 127.45 (C-5 or 6), 23.0 (C-7). IR (CDCl3) nu (cm?1)=3339, 2982, 2920, 2866, 1889, 1695, 1674, 1573, 1448, 1373, 1237, 1031, 912, 779, 690, 536. HRMS (GC FI, 10,000V) calculated for C8H7BrO [M+·] 197.96803, found 197.96767 (Diff.: ?1.80ppm). Mp=50°C. |
89% | With pyridinium chlorochromate; In dichloromethane; at 20℃; | [00203] A flask was charged with (2-bromo-3-methylphenyl)methanol (5.00 g, 24.9 mmol, 1.00 equiv), pyridinium chlorochromate (16.2 g, 75.0 mmol, 3.00 equiv), and DCM (70 mL). The resulting solution was stirred overnight at rt and concentrated. The residue was chromatographed on a silica gel column (20:80 EtOAc/petroleum ether) to provide 2-bromo-3-methylbenzaldehyde (4.40 g, 89percent yield) as a white solid. GCMS (EI, m/z): 198 [M]+. |
With manganese(IV) oxide; In chloroform; | Example 67Synthesis of N-[(E)-3-(4'-hydroxy-6-methyl-biphenyl-2-yl)-2-methyl-acryloyl]-guanidine<Step 1>2-methyl-3-bromobenzoic acid (1 g, 4.65 mmol) and triethylamine (0.97 mL, 6.78 mmol) were dissolved in THF (20 mL), chloroformic acid ethyl (0.49 mL, 6.11 mmol) was added thereto while cooling it by ice and then stirred for 15 minutes. The precipitate was then eliminated by suction filtration, 1 g of ice and sodium borohydride (260 mg, 6.78 mmol) were added to the resulting filtrate while cooling it by ice and then stirred overnight. It was washed with water and saturated saline and then dried over anhydrous MgSO4. The solvent was then eliminated in vacuo to obtain a residue. The resulting residue was dissolved in chloroform (50 mL), manganese dioxide (2 g, 22.5 mmol) was added thereto and then stirred overnight. After filtration, the solvent was eliminated in vacuo and then purified by reversed phase HPLC (0.1percent TFA in water/CH3CN) to obtain an aldehyde (640 mg, 69percent).MS: 199 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; 1,3-dimethylimidazolim iodide; In tetrahydrofuran; for 0.5h;Reflux; | To a mixture of 4-chloro-2-(methylthio)pyrimidine (0.36 mL, 3.11 mmol), 2- bromo-3-methylbenzaldehyde (0.744 g, 3.74 mmol), and l,3-dimethyl-l//-imidazol-3- ium iodide (0.697 g, 3.11 mmol) in THF (3 mL) was added NaH (0.149 g, 3.74 mmol) and the resulting mixture was refluxed for 30 min. Product was observed and the reaction went to completion. The mixture was brought to RT and poured into ice-water, extracted with DCM and purified using hexanes to afford a light yellow solid as (2-bromo-3- methylphenyl)(2-(methylthio)pyrimidin-4-yl)methanone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of 2-iodopyrazine (0.48 mL, 4.85 mmol) in dry THF (3 mL) was brought to 0 °C followed by the slowly addition of butylmagnesium chloride, 2.0M solution in THF (2.4 mL, 4.85 mmol). The resulting dark solution was stirred at 0°C for 30 min then a solution of <strong>[109179-31-9]2-bromo-3-methylbenzaldehyde</strong> (1.06 g, 5.34 mmol) in THF (2 mL) was slowly added and kept at 0 °C for 2 h. The mixture was quenched with saturated NH4C1 and extracted with DCM. The combined organics were washed with brine, dried over Na2S04, filtered, concentrated and purified by silica gel column chromatography using gradient 1 :1 hexanes/EtOAc to affrod a yellow-orange oil as (2-bromo-3- methylphenyl)(pyrazin-2-yl)methanol. |
Tags: 109179-31-9 synthesis path| 109179-31-9 SDS| 109179-31-9 COA| 109179-31-9 purity| 109179-31-9 application| 109179-31-9 NMR| 109179-31-9 COA| 109179-31-9 structure
A163297 [400822-47-1]
4-Bromo-3,5-dimethylbenzaldehyde
Similarity: 0.97
A163297 [400822-47-1]
4-Bromo-3,5-dimethylbenzaldehyde
Similarity: 0.97
A163297 [400822-47-1]
4-Bromo-3,5-dimethylbenzaldehyde
Similarity: 0.97
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