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[ CAS No. 586374-04-1 ]

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2D
Chemical Structure| 586374-04-1
Chemical Structure| 586374-04-1
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Product Details of [ 586374-04-1 ]

CAS No. :586374-04-1MDL No. :MFCD10698751
Formula : C9H9FO2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :168.17Pubchem ID :22049929
Synonyms :

Computed Properties of [ 586374-04-1 ]

TPSA : 26.3 H-Bond Acceptor Count : 3
XLogP3 : 2.2 H-Bond Donor Count : 0
SP3 : 0.22 Rotatable Bond Count : 2

Safety of [ 586374-04-1 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P305+P351+P338UN#:N/A
Hazard Statements:H227-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 586374-04-1 ]

  • Upstream synthesis route of [ 586374-04-1 ]
  • Downstream synthetic route of [ 586374-04-1 ]

[ 586374-04-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 67-56-1 ]
  • [ 315-31-1 ]
  • [ 586374-04-1 ]
YieldReaction ConditionsOperation in experiment
83% at 0℃; Reflux Step A: To a stirred solution of 2-fluoro-3-methylbenzoic acid (4.0 g, 26.0 mmol) in anhydrous methanol (52 mL) at 0 °C was added thionyl chloride (2.8 mL, 39.0 mmol) dropwise and the reaction mixture was stirred overnight at reflux. The mixture was diluted with methanol and concentrated under reduced pressure to remove the excess thionyl chloride. The residue was then dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate, dried (Na2SO,*), filtered, and concentrated under reduced pressure to give methyl 2-fluoro-3-methylbenzoate (3.6 g, 83percent) as a clear oil that was used in the next step without further purification: 1H NMR (500 MHz, CDCl3) δ 7.75- 7.72 (m, I H), 7.38-7.35 (m, I H), 7.26-7.06 (m, I H), 3.91 (s, 3H), 2.31 (s, 3H).
82% for 2 h; Heating / reflux To a solution of 2- fluoro-3-methyl benzoic acid (3.57 g, 23 mmol) in MeOH (40 mL) was added concentrated sulfuric acid (2.3 mL), and the reaction mixture was heated at reflux for 12 h. The reaction mixture was cooled, the solvent was removed under reduced pressure, and the residue was dissolved in EtOAc. The organic solution was washed with a saturated solution OF NAHC03 and then brine, dried (NA2SO4), filtered and concentrated under reduced pressure to afford methyl 2-FLUORO-3-METHYLBENZOATE as a yellow oil (3.2 g, 82percent): H NMR (300 MHz, CDC13) 8 7.76-7. 71 (m, 1H), 7.39-7. 34 (m, 1H), 7. 08 (t, J = 8 Hz, 1H), 3.98 (s, 3H), 2.31 (d, J = 3 HZ, 3H).
82% for 2 h; Heating / reflux To a solution of 2- fluoro-3-methyl benzoic acid (3.57 g, 23 mmol) in MeOH (40 mL) was added concentrated sulfuric acid (2.3 mL), and the reaction mixture was heated at reflux for 12 h. The reaction mixture was cooled, the solvent was removed under reduced pressure, and the residue was dissolved in EtOAc. The organic solution was washed with a saturated solution OF NAHC03 and then brine, dried (NA2SO4), filtered and concentrated under reduced pressure to afford methyl 2-FLUORO-3-METHYLBENZOATE as a yellow oil (3.2 g, 82percent): H NMR (300 MHz, CDC13) 8 7.76-7. 71 (m, 1H), 7.39-7. 34 (m, 1H), 7. 08 (t, J = 8 Hz, 1H), 3.98 (s, 3H), 2.31 (d, J = 3 HZ, 3H).
Reference: [1] Patent: WO2011/8572, 2011, A2, . Location in patent: Page/Page column 62
[2] Patent: WO2005/18557, 2005, A2, . Location in patent: Page/Page column 304
[3] Patent: WO2005/18557, 2005, A2, . Location in patent: Page/Page column 304
  • 2
  • [ 22223-49-0 ]
  • [ 586374-04-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4416 - 4420
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