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[ CAS No. 15365-25-0 ]

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Chemical Structure| 15365-25-0
Chemical Structure| 15365-25-0
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CAS No. :15365-25-0 MDL No. :MFCD04114316
Formula : C10H11BrO3 Boiling Point : 350.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :259.10 g/mol Pubchem ID :139928
Synonyms :

Safety of [ 15365-25-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 15365-25-0 ]

  • Upstream synthesis route of [ 15365-25-0 ]
  • Downstream synthetic route of [ 15365-25-0 ]

[ 15365-25-0 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
100% With N-Bromosuccinimide In tetrachloromethane for 2 h; Reflux To a solution of methyl 4-methoxy-2-methylbenzoate (1 g, 5.6 mmol) in CC14 (25 mL) was added dropwise N-bromosuccinimide (1.1 g, 6.2 mmol) previously dissolved in CCI4 (5 mL) and a catalytic amount of benzoylperoxide. The mixture was refluxed for 2 hours, cooled to room temperature and poured onto ice water. The aqueous mixture was extracted with DCM (3x), and the combined organics were dried over MgS04, filtered, and concentrated in vacuo to provide 2.1 g of the titled product as light yellow solid (~ 100percent yield): [M+H+] m/z 260.
100% With N-Bromosuccinimide In tetrachloromethane for 2 h; Reflux [00121] Step 1 : Methyl 2-(bromomethyl)-4-methoxybenzoate[00122] To a solution of methyl 4-methoxy-2-methylbenzoate (1 g, 5.6 mmol) inCC14 (25 mL) was added dropwise N-bromosuccinimide (1.1 g, 6.2 mmol) previously dissolved in CC14 (5 mL) and a catalytic amount of benzoyl peroxide. The mixture was refluxed for 2 hours, cooled to room temperature and poured onto iced water. The aqueous mixture was extracted with DCM (3x), and the combined organics were dried over MgS04, filtered, and concentrated in vacuo to provide 2.1 g of the titled product as light yellow solid (~ 100percent yield): [M+H+] m/z 260.
68% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2.5 h; Heating / reflux To a solution of 4-methoxy-2-methyl-benzoic acid methyl ester (1.47 g, 8.16 mmol, 1.0 equiv; commercially available) in CCl4 (15 mL) was added N-bromosuccinimide (1.60 g, 8.97 mmol, 1.1 equiv) and dibenzoyl peroxide (0.198 g, 0.45 mmol, 0.05 equiv). The mixture was heated to reflux for 1.5 h, when TLC indicated that still some starling material was left. Therefore, additional N-bromosuccinimide (0.16 g, 0.90 mmol, 0.11 equiv) and dibenzoyl peroxide (0.080 g, 0.41 mmol, 0.18 equiv) was added and heating continued for 1 h. The reaction mixture was cooled down, poured on crashed ice, extracted with ethyl acetate, the combined organic phases washed with a sat. solution of NaCl, dried over Na2SO4 and concentrated by evaporation under reduced pressure. The crude material was purified with silica column chromatography eluting with hexane/ethyl acetate (95:5) affording 1.43 g (68percent) of the title compound as yellow crystals. 1H NMR (300 MHz, CDCl3): δ 3.87 (s, 3H), 3.91 (s, 3H), 4.97 (s, 2H), 6.86 (dd, J=8.7 Hz, J=2.7 Hz, 1H), 6.97 (d, J=2.7 Hz, 1H), 7.99 (d, J=8.7 Hz, 1H).
62% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 18 h; Heating / reflux 2-Bromomethyl-4-methoxy-benzoic acid methyl esterTo a solution of 4-Methoxy-2-methyl-benzoic acid methyl ester (6.92g, 38.4 mmol) in CCI4 (100 mL) was added N-bromosuccinimide (7.99 g, 1.17 mmol). Benzoyl peroxide (1.82 g, 7.54 mmol) was added to the slurry and the mixture was heated at reflux for 18 h. The reaction was cooled and the solid was filtered off. The filtrate was absorbed onto silica to perform chromatography (0-10 percent ethyl acetate/hexanes) to yield 2-Bromomethyl-4-methoxy- benzoic acid methyl ester, (6.12 g, 62 percent, CASNo. 15365-25-0). MS: ES M+1 : 258.9, M+2 260.9 (258.0, 260.0).
60% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 24 h; Reflux Methyl 2-methyl-4-(methyloxy)benzoate (1.1 g, 6.1 mmol), N-bromosuccinimide (1.2 g, 6.74 mmol), benzoyl peroxide (0.073 g, 0.30 mmol), and carbon tetrachloride (40 mL) were combined and the stirred reaction mixture was heated at reflux for 24 h under a nitrogen atmosphere. The reaction mixture was allowed to cool at room temperature and filtered through a pad of Celite.(R).. The pad was washed with ethyl acetate. The filtrate was concentrated to give the crude product which was purified by flash chromatography over silica with a hexanes:dichloromethane gradient (100:0 to 50:50) to give 0.95 g (60percent) of methyl 2-(bromomethyl)-4-(methyloxy)benzoate as an oil which solidified to a white solid. 1U NMR (400 MHz, CDCl3): δ 7.98 (d, J = 9 Hz, IH), 6.96 (d, J = 3 Hz, IH), 6.85 (dd, J = 9, 3 Hz, IH), 4.96 (s, 2H), 3.90 (s, 3H), 3.86 (s, 3H).
58% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4.5 h; UV-irradiation; Heating / reflux A mixture of 4-methoxy-2-methyl-benzoic acid methyl ester (20 g, 111 mmol), N-bromo- succinimide (20.7 g, 117 mmol) and dibenzoylperoxide (0.54 g, 2 mmol) in [CC14] (150 mL) was irradiated with a 300 W lamp. The reaction maintains a steady reflux and after 4.5 h, the lamp was removed and the mixture cooled to [5 C.] The mixture was then filtered, the filtrate evaporated and the residue purified twice by chromatography [(SI02,] Heptane: Di- ethyl ether: 95: 5 to 85: 15) to afford the title product (16.6 g, 58percent) as a white solid. MS m/e = 258.1 (M-H+).

Reference: [1] Patent: WO2011/85261, 2011, A1, . Location in patent: Page/Page column 36
[2] Patent: WO2011/85128, 2011, A1, . Location in patent: Page/Page column 56
[3] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1798 - 1806
[4] Patent: US2008/249101, 2008, A1, . Location in patent: Page/Page column 40
[5] Patent: WO2008/20306, 2008, A2, . Location in patent: Page/Page column 35
[6] Patent: WO2009/5998, 2009, A1, . Location in patent: Page/Page column 214
[7] Patent: WO2004/14856, 2004, A1, . Location in patent: Page 9; 14
[8] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 1912 - 1918
[9] Patent: WO2006/19768, 2006, A1, . Location in patent: Page column 90
[10] Patent: WO2006/20879, 2006, A1, . Location in patent: Page/Page column 62-63
[11] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 5, p. 1628 - 1631
[12] Journal of Medicinal Chemistry, 2012, vol. 55, # 8, p. 3975 - 3991
[13] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 360 - 365
[14] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8561 - 8578
[15] Inorganic Chemistry, 2014, vol. 53, # 6, p. 2932 - 2942
[16] Tetrahedron, 2017, vol. 73, # 20, p. 2913 - 2922
[17] Tetrahedron, 2018, vol. 74, # 2, p. 224 - 239
[18] ChemMedChem, 2018, vol. 13, # 15, p. 1530 - 1540
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Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1798 - 1806
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 360 - 365
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8561 - 8578
[4] Inorganic Chemistry, 2014, vol. 53, # 6, p. 2932 - 2942
[5] Tetrahedron, 2018, vol. 74, # 2, p. 224 - 239
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Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1798 - 1806
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  • [ 15365-25-0 ]
Reference: [1] Inorganic Chemistry, 2014, vol. 53, # 6, p. 2932 - 2942
  • 5
  • [ 15365-25-0 ]
  • [ 252061-66-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 8, p. 3975 - 3991
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