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[ CAS No. 18980-21-7 ] {[proInfo.proName]}

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Chemical Structure| 18980-21-7
Chemical Structure| 18980-21-7
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Product Details of [ 18980-21-7 ]

CAS No. :18980-21-7 MDL No. :MFCD00055489
Formula : C8H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :MAAADQMBQYSOOG-UHFFFAOYSA-N
M.W : 201.06 Pubchem ID :87877
Synonyms :

Safety of [ 18980-21-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310+P330 UN#:2810
Hazard Statements:H301 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 18980-21-7 ]

* 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.

  • Upstream synthesis route of [ 18980-21-7 ]
  • Downstream synthetic route of [ 18980-21-7 ]

[ 18980-21-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 18980-21-7 ]
  • [ 74-88-4 ]
  • [ 33839-11-1 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 16 h; 4-Bromo-2-ethyl-l-methoxybenzeneTo a slurry of 4-bromo-2-ethylphenol (0.500 g, 2.49 mmol) and sodium hydride (0.149 g, 3.73 mmol) in DMF (2.487 mL) cooled to 0 0C was added iodomethane (0.310 mL, 4.97 mmol). The reaction mixture solidified so DMF (1.970 ml) was added and the reaction stirred at ambient temperature for 16 hours. The reaction mixture was quenched with 2M NaOH (25 mL), diluted with EtOAc (75 mL) and washed sequentially with 2M NaOH (25 mL) and saturated brine (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 10 to 20percent EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 4-bromo-2-ethyl-l-methoxybenzene (0.485 g, 91 percent) as a colourless oil.MS (+ve ESI) : Rt = 3.03 min, no mass ion (M+H)+ 1H NMR (400.13 MHz, CDC13) δ 1.17 (3H, t), 2.60 (2H, q), 3.80 (3H, s), 6.68 - 6.71 (IH, m), 7.24 - 7.26 (2H, m)
68% With potassium carbonate In DMF (N,N-dimethyl-formamide) for 16 h; H NMR (CDC13) : No. 1. 17 (t, 3H, J = 7. 4 Hz), 2.59 (q, 2H, J= 7.4 Hz), 3.80 (s, 3H), 6.70 (d, 1H, J= 8.8 Hz), 7.26 (m, 2H). Potassium carbonate (3.9g, 28. 3MMOL) and methyl iodide (0.59mL, 9. 43MMOL) were added to a solution of 4-Bromo-2-ethyl-phenol (1.9g, 9. 43MMOL, from step 1 of Example A (22)) dissolved in DMF (10ML). The mixture was stirred for 16 h under N2 and then partitioned between 1 N HCI and EtOAc. The organic layer was washed with saturated NAHC03, brine, dried over NA2SO4 and concentrated to a yellow oil. The oil was purifed by silica gel chromatography to give the title compound as a clear oil (1.37g, 68percent).
Reference： [1] Patent: WO2009/1127, 2008, A1, . Location in patent: Page/Page column 270
[2] Patent: WO2004/74270, 2004, A2, . Location in patent: Page 127-128
  • 2
  • [ 18980-21-7 ]
  • [ 77-78-1 ]
  • [ 33839-11-1 ]
Reference： [1] Journal of medicinal chemistry, 1971, vol. 14, # 9, p. 789 - 792
[2] Bulletin de la Societe Chimique de France, 1969, p. 781 - 787
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