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Chemical Structure| 1260857-12-2 Chemical Structure| 1260857-12-2

Structure of 1260857-12-2

Chemical Structure| 1260857-12-2

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Product Details of [ 1260857-12-2 ]

CAS No. :1260857-12-2
Formula : C8H5Br2ClO
M.W : 312.39
SMILES Code : ClC1=CC=C(Br)C(=C1)C(=O)CBr
MDL No. :MFCD11847058

Safety of [ 1260857-12-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 1260857-12-2 ]

* 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 [ 1260857-12-2 ]

[ 1260857-12-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 935-99-9 ]
  • [ 1260857-12-2 ]
YieldReaction ConditionsOperation in experiment
With aluminum (III) chloride; bromine; In tetrahydrofuran; at 0 - 20℃; for 3.5h;Inert atmosphere; General procedure: The title compd was prepared as per Scheme 3 (steps a-b). Step a: To a solution of 2?-bromoacetophenone 46 (100 g, 0.50 mol), in THF (100 mL) at 0 °C was added AlCl3 (3.37 g, 0.025 mol) followed by dropwise addition of Br2 (28.3 mL, 0.552 mol) over 90 min. The mixture was then allowed to warm to rt and stirred for 2 h whereupon it was quenched by addition of water (500 mL) and extracted with EtOAc (3×300 mL). (Note: the first extract is denser than water due to concentration.)The combined organic layer washed with brine(2×400 mL), dried (MgSO4), filtered and concentrated in vacuo toobtain 2-bromo-(2?-bromoacetophenone) as yellow oil (215.4 g) and was used as crude. The 2-bromo-(2?-bromoacetophenone) (176.9 g, 0.414 mol) thus obtained was dissolved in ethanol (1.8 L) and 1-cyclopropylthiourea 20 (48 g, 0.414 mol) and the mixture refluxed for 2 h then allowed to cool to rt and the mixture concentrated to ?150 mL whereupon diethyl ether (2.2 L) was added with rapid stirring resulting in a precipitate that was filtered and air-dried to obtain the HBr salt ofthe desired product (145 g). This salt was then suspended in DCM (1.1L) and washed with saturated NaHCO3 (2×900 mL) to free base the product. The organic layer was dried (Na2SO4), filtered and concentrated to obtain 48 as an off-white solid (101 g, 83percent). LCMS(Method B) m/z 296 (M+1). HPLC purity > 98percent (254 nm). 1H NMR(CDCl3) delta: 7.69 ? 7.62 (m, 2H), 7.35 ? 7.29 (m, 1H), 7.19 ? 7.11 (m,1H), 6.91 (s, 1H), 6.56 (bs, 1H), 2.60 ? 2.53 (m, 1H), 0.72 ? 0.65 (m,2H), 0.62 ? 0.56 (m, 2H). Step b: A mixture of 48 (1g, 3.39mmol), aq 2M K2CO3 (5.1mL, 10.2mmol), 6-methoxypyridine-3-boronic acid (1.04g, 6.78mmol) and toluene (30mL) was degassed with Ar for 10min. Pd2(dba)3 (0.31g, 0.34mol) and S-Phos (0.28g, 0.68mmol) were then added and the mixture heated to 85°C for 90min. After allowing the mixture to cool to rt the reaction mixture was diluted with EtOAc (100mL) and washed with brine (50mL). The aq layer was further extracted with EtOAc (2*50mL) and then the combined extracts dried (MgSO4), filtered and concentrated in vacuo. The crude (brown viscous oil) was purified by flash chromatography using 20-50percent EtOAc in cyclohexane to obtain 50 as yellow solid (0.99g, 90percent). LCMS (Method B) m/z 324 (M+1). HPLC purity>98percent (254nm). 1H NMR (CDCl3) delta: 7.73 (d, J=2.6Hz, 1H), 7.55 (d, J=8.5Hz, 1H), 7.12 (dd, J=2.6, 8.5Hz, 1H), 7.00 (bs, 1H), 2.59 - 2.55 (m, 1H), 0.74 - 0.69 (m, 2H), 0.63 - 0.59 (m, 2H).
 

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