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Chemical Structure| 168886-97-3 Chemical Structure| 168886-97-3

Structure of 168886-97-3

Chemical Structure| 168886-97-3

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Product Details of [ 168886-97-3 ]

CAS No. :168886-97-3
Formula : C8H9BrO
M.W : 201.06
SMILES Code : OCC1=CC=CC(C)=C1Br
MDL No. :MFCD16659614
InChI Key :KOMJECHMWYAILT-UHFFFAOYSA-N
Pubchem ID :52987706

Safety of [ 168886-97-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 168886-97-3 ]

* 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 [ 168886-97-3 ]

[ 168886-97-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 168886-97-3 ]
  • [ 109179-31-9 ]
YieldReaction ConditionsOperation 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
 

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