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[ CAS No. 251458-15-8 ]

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Chemical Structure| 251458-15-8
Chemical Structure| 251458-15-8
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CAS No. :251458-15-8 MDL No. :MFCD13192201
Formula : C11H13BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :257.12 g/mol Pubchem ID :24777892
Synonyms :

Safety of [ 251458-15-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 251458-15-8 ]

  • Upstream synthesis route of [ 251458-15-8 ]
  • Downstream synthetic route of [ 251458-15-8 ]

[ 251458-15-8 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 150529-73-0 ]
  • [ 74-88-4 ]
  • [ 251458-15-8 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 50℃; for 2 h; Inert atmosphere
Stage #2: at 20 - 40℃;
Sodium hydride (60percent in oil) (10.4 g, 436 mmol) was added to tetrahydrofuran (400 ml) under argon and heated with stirring to 50° C. Methyl 2-(3-bromophenyl)acetate (20 g, 87.3 mmol) was added drop wise over 30 minutes and heating continued for 90 minutes.
The temperature was lowered to below 40° C. and methyl iodide (13 ml, 209 mmol) was added over 10 minutes.
The resulting suspension was stirred at room temperature overnight.
Water (300 ml) was carefully added and reaction mixture concentrated.
Residue was partitioned between diethyl ether (400 ml) and water.
The aqueous layer was extracted with diethyl ether (400 ml), and the combined ethereal extracts were dried over sodium sulfate and concentrated.
Crude oil was purified by column chromatography, eluding with a gradient from 0percent to 20percent ethyl acetate in heptane to give methyl 2-(3-bromophenyl)-2-methylpropanoate (14.96 g, 58 mmol, 67percent).
1H NMR (400 MHz, CDCl3): δ ppm 7.47 (t, 1H), 7.37 (dt, 1H), 7.24 (dt, 1H), 7.18 (t, 1H), 3.65 (s, 3H), 1.55 (s, 6H)
51%
Stage #1: With sodium hydride In tetrahydrofuran for 0.25 h;
Stage #2: at 20℃;
Example 4A: methyl 2-(3-bromophenyl)-2-methylpropanoate j00218j Example 5A (154 mg, 0.672 mmol) was dissolved in THF (2.24 mL). Sodium hydride (46.8 mg, 1.95 mmol) was added and the reaction was stirred for 15 minutes.Methyl iodide (807 iL) was added and the reaction was allowed to stir overnight at ambient temperature. The reaction was quenched with water and extracted twice with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was purified by silica gel column chromatography (0 to 100percent EtOAc in hexanes) to yield Example 4A (87.5 mg, 51percent) as aclear oil. 1H NMR (400 MHz, CHLOROFORM-d) ö ppm 7.48 (1 H, t, J=1.88 Hz), 7.37 (1 H, dt, J=7.78, 1.51 Hz), 7.23 - 7.28 (1 H, m), 7.20 (1 H, d, J=7.78 Hz), 3.65 (3 H, s), 1.56(6 H, s).
Reference: [1] Patent: US2010/197591, 2010, A1, . Location in patent: Page/Page column 15-16
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 3, p. 392 - 395
[3] Patent: US2005/80111, 2005, A1,
[4] Patent: WO2014/201073, 2014, A1, . Location in patent: Paragraph 00218
[5] Patent: WO2004/48374, 2004, A1, . Location in patent: Page 47
[6] Patent: WO2010/52448, 2010, A2, . Location in patent: Page/Page column 36
  • 2
  • [ 74-88-4 ]
  • [ 251458-15-8 ]
Reference: [1] Patent: US2006/149070, 2006, A1, . Location in patent: Page/Page column 37
[2] Patent: WO2007/87448, 2007, A1, . Location in patent: Page/Page column 34; 35
  • 3
  • [ 90433-20-8 ]
  • [ 251458-15-8 ]
YieldReaction ConditionsOperation in experiment
36% With acetic acid In sulfuric acid; water a
2-Methyl-2-[3-bromophenyl]propionic Acid Methyl Ester
2-Methyl-2-[3-bromophenyl]propionitrile (0.56 g, 2.5 mmol) was refluxed in sulfuric acid (2 ml), water (3 ml) and acetic acid (2.5 ml) overnight.
The reaction mixture was poured in water, then extracted with Et2O.
The combined organic extracts were dried with magnesium sulfate, filtered, concentrated, and chromatographed (silica gel, 10percent EtOAc, 1percent HOAc) to give the title compound as a white solid (0.2 g, 36percent), which was converted to the methyl ester with diazo methane in Et2O and was used in the next reaction without further purification.
Reference: [1] Patent: US6518267, 2003, B1,
  • 4
  • [ 251458-15-8 ]
  • [ 81606-47-5 ]
YieldReaction ConditionsOperation in experiment
68%
Stage #1: With methanol; sodium hydroxide In tetrahydrofuran for 2 h; Reflux
Stage #2: With hydrogenchloride In water
INTERMEDIATE 82-(3 -Bromophenyl)-2-methylpropionic acidSodium hydroxide (2M, 20 mL) was added to a solution of Intermediate 7 (6.5 g) in MeOH (20 mL) and THF (20 mL). The resulting mixture was refluxed for 2 h. The mixture was evaporated, and the residue partitioned between water and DCM (100 mL each). The aqueous phase was acidified (2M hydrochloric acid) and extracted with DCM (100 mL then 50 mL). The combined organic phases were dried (MgSO4) and the solvent removed in vacuo to give the title compound (4.55 g, 68percent over two steps) as a cream solid. δH (CDCl3) 7.54 (s, IH), 7.40 (d, IH), 7.33 (d, IH), 7.21 (t, IH), 1.59 (s, 6H).
Reference: [1] Patent: WO2010/52448, 2010, A2, . Location in patent: Page/Page column 37
[2] Patent: WO2004/48374, 2004, A1, . Location in patent: Page 47
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