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Chemical Structure| 78504-28-6 Chemical Structure| 78504-28-6

Structure of 78504-28-6

Chemical Structure| 78504-28-6

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Product Details of [ 78504-28-6 ]

CAS No. :78504-28-6
Formula : C14H13BrO2
M.W : 293.16
SMILES Code : COC1=C(OCC2=CC=CC=C2)C=C(Br)C=C1
MDL No. :MFCD09836381
InChI Key :OFFXGGNLPNBCBO-UHFFFAOYSA-N
Pubchem ID :14912852

Safety of [ 78504-28-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501

Application In Synthesis of [ 78504-28-6 ]

* 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 [ 78504-28-6 ]

[ 78504-28-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 78504-28-6 ]
  • [ 243990-54-7 ]
YieldReaction ConditionsOperation in experiment
[311.2] 4.86 g of 2-Benzyloxy-4-bromo-1-methoxybenzene was dissolved in 100 ml of anhydrous tetrahydrofuran and cooled to -78C in a nitrogen atmosphere. 15 ml of 1.6 M n-butyl lithium in hexane was added dropwise, and the mixture was stirred for 30 minutes. 6 ml of Triisopropoxy borate was added all at once, and the mixture was allowed to warm overnight at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was dissolved in 1N aqueous sodium hydroxide and extracted with diethyl ether. The aqueous layer was neutralized with 5N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated to give 1.76 of the title compound.1H-NMR(CDCl3) δ: 3.76 (s, 3H) 5.04 (s, 2H) 6.93 (d, J=8.0Hz, 1H) 7.31-7.46 (m, 6H) 7.86 (s, 1H)
  • 2
  • [ 121-43-7 ]
  • [ 78504-28-6 ]
  • [ 243990-54-7 ]
YieldReaction ConditionsOperation in experiment
80% 4-Bromo-3-methoxyphenol 25 (0.682 mmol, 0.200 g) was dissolved in freshly distilled THF (7 mL) in an oven-dried three-neck flask under argon.The temperature was cooled to 78 C and the solution was stirred for 30 min before dropwise addition of n-BuLi (1.6 N in hexanes,0.752 mmol, 0.470 mL). Once the addition of n-BuLi was completed, the mixture was stirred for another 30 min at 78 C beforethe dropwise addition of trimethyl borate (2.05 mmol, 0.233 mL).The reaction mixture was allowed to warm to room temperatureand stirred for 5 h. The temperature was cooled to 20 C andHCl 1 N was slowly added to reach pH = 2-3. The reaction mixture was allowed to warm to room temperature and extracted threetimes with EtOAc. The organic layers were combined, washed withbrine, dried with MgSO4 and concentrated in vacuo until precipitation occurred. Hexanes was then added to maximize precipitation.The solution was filtered and the solid was dried under vacuum.The precipitation/filtration procedure was repeated twice, giving42 as a white solid in an 80% yield (0.543 mmol, 0.140 g).mp = 135-155 C. 1H NMR (500 MHz, CDCl3): dH 7.80 (1H, d,J = 8.0), 7.70 (1H, s), 7.58-7.29 (6H, m), 7.04 (1H, d, J = 8.0), 5.28(2H, s), 3.99 (3H, s). 13C NMR (125 MHz, CDCl3): dC 153.6, 147.7,137.2, 130.3, 128.6, 127.9, 127.5, 120.5, 111.0, 71.3, 55.9. 11BNMR (160 MHz, CDCl3): dB 28.6. IR (ATR, ZnSe): mmax 1595, 1410,1319, 1250, 1216, 1179, 1133, 1018, 740, 710 cm1. HRMS (ESITOF,m/z): calcd for C14H14BO3 (M-H2O+H)+ = 241.1031, found 241.1049
 

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