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Chemical Structure| 765-56-0 Chemical Structure| 765-56-0

Structure of 765-56-0

Chemical Structure| 765-56-0

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Product Details of [ 765-56-0 ]

CAS No. :765-56-0
Formula : C5H5BrO
M.W : 161.00
SMILES Code : O=C1C=CC(Br)C1
MDL No. :MFCD20621210

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Application In Synthesis of [ 765-56-0 ]

* 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 [ 765-56-0 ]

[ 765-56-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 42726-73-8 ]
  • [ 765-56-0 ]
  • [ 110027-65-1 ]
YieldReaction ConditionsOperation in experiment
80% A solution of NaOMe (151 mg, 2.80 mmol) in THF/MeOH (2 mL : 5 mL) was added slowly to a stirred solution of bromide (9) (322 mg, 2.0 mmol) and <strong>[42726-73-8]tert-butyl methyl malonate</strong> (0.35 mL, 2.05 mmol) in THF (8 mL) at room temperature, and the resulting mixture stirred for 65 min. The reaction was quenched with 1 M hydrochloric acid (2 mL) and diluted with H2O (10 mL) before volatile materials were removed under reduced pressure. The resulting solution was extracted with EtOAc (3 x 10 mL), and the combined organic layers dried over MgSO4 and concentrated under reduced pressure. Purification by silica chromatography (EtOAc/hexane, 1:1) gave malonic ester (11) (392 mg, 80percent) as an oil consisting of an inseparable 8:7 mixture of diastereoisomers.(Both diastereoisomers): Rf 0.45 (EtOAc/hexane, 1:1). MS (MH+, ESI): 255.2 (Calc. MH+ 255.1232). IR (numax/cm-1): 2958, 1734, 1730, 1714, 1586.(Major diastereoisomer): 1H NMR (400 MHz, CDCl3, ppm): 7.62 (dd, J = 5.7, 2.4, 1H, HC=CHCO); 6.16 (J = 5.7, 1.4, 1H, HC=CHCO); 3.68 (s, 3H, CO2CH3); 3.52 (m, 1H, CHCH(CO2R)2); 3.33 (d, J = 13.5, 1H, CH(CO2R)2); 2.54 (dd, J = 19.0, 1.8, 1H, COCHAHB); 2.21 (dd, J = 19.0, 1.2, 1H, COCHAHB); 1.39 (s, 9H, C(CH3)3).(Minor diastereoisomer): 1H NMR (400 MHz, CDCl3, ppm): 7.62 (dd, J = 5.7, 2.4, 1H, HC=CHCO); 6.16 (J = 5.7, 1.4, 1H, HC=CHCO); 3.69 (s, 3H, CO2CH3); 3.52 (m, 1H, CHCH(CO2R)2); 3.33 (d, J = 13.5, 1H, CH(CO2R)2); 2.54 (dd, J = 19.0, 1.8, 1H, COCHAHB); 2.21 (dd, J = 19.0, 1.2, 1H, COCHAHB); 1.38 (s, 9H, C(CH3)3)
 

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