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[ CAS No. 4897-84-1 ]

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CAS No. :4897-84-1 MDL No. :MFCD00041482
Formula : C5H9BrO2 Boiling Point : 186.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :181.03 g/mol Pubchem ID :107604
Synonyms :

Safety of [ 4897-84-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 4897-84-1 ]

  • Upstream synthesis route of [ 4897-84-1 ]
  • Downstream synthetic route of [ 4897-84-1 ]

[ 4897-84-1 ] Synthesis Path-Upstream   1~15

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Reference: [1] Patent: US2003/181498, 2003, A1,
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YieldReaction ConditionsOperation in experiment
86%
Stage #1: With hydrogen bromide In acetic acid at 75℃; for 4 h;
Stage #2: at 20℃;
A solution of γ-butyrolactone (25 mL, 28.0 g, 0.325 mole) in a 45percent solution of hydrogen bromide in acetic acid (75 mL) was heated for 4 h at 75° C., cooled to room temperature, treated with methanol (150 mL), and stirred overnight. Evaporation of the solvent gave a dark oil, which was dissolved in ethyl acetate (150 mL) and washed successively with saturated sodium bicarbonate (2.x.150 mL), saturated sodium chloride (150 mL), dried over anhydrous magnesium sulfate, and evaporated to yield a clear oil (48.8 g, 86percent). 1Hmr (CDCl3, δ): 3.68 (3H, s, OCH3), 3.44 (2H, t, 6.4 Hz, CH2γ), 2.51 (2H, t, 7.2 Hz, CH2α), 2.17 (2H, quintet, 6.8 Hz, CH2β). 13Cmr (CDCl3, δ): 172.96, 51.70, 32.66, 32.19, 27.70. IR (neat): 1738 cm-1. Mass spectrum (CI, m/z): 181 (M+1), 183 (M+3). Calcd. for C5H9O2Br: C, 33.17; H, 5.02. Found: C, 32.62; H, 4.85.
Reference: [1] Helvetica Chimica Acta, 1980, vol. 63, # 8, p. 2508 - 2514
[2] Canadian Journal of Chemistry, 2003, vol. 81, # 8, p. 937 - 960
[3] Patent: US2003/232820, 2003, A1, . Location in patent: Page 13
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 336 - 343
[5] Chemistry - An Asian Journal, 2018, vol. 13, # 4, p. 409 - 412
[6] Archiv der Pharmazie (Weinheim, Germany), 1958, vol. 291, p. 23,25, 32
[7] Synthesis, 1982, # 11, p. 963 - 965
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YieldReaction ConditionsOperation in experiment
100% at 0 - 20℃; for 18 h; Inert atmosphere Acetyl chloride (576 mg, 550 μL, 7.34 mmol) was added to a solution of 4-bromobutyric acid 4 (5.00 g, 30.0 mmol) in methanol (40 mL) cooled to 0 °C. The resulting solution was allowed to warm to room temperature and stirred for 18 h. The solution was evaporated under reduced pressure to yield methyl 4-bromobutanoate 5 (5.40 g, 30.0 mmol quant.) as acolourless oil, which was used without any further purification
85% at 0 - 20℃; Inert atmosphere Example 29: Synthesis of 4- (nitrooxy) butanoic acidO oNo2 STEP A: methyl 4-bromobutanoateTo a solution of 4-bromobutanoic acid (6.5 g, 38.9 mmol) in MeOH (120 mL) at 0°C under nitrogen atmosphere, thionyl chloride (2.8 mL, 38.9 mmol) was slowly added and the reaction was stirred overnight at room temperature Solvent was evaporated and the crude material was used directly in next step. (6.0 g, 85percent) H-NMR (CDCI3) : 3.71 (3H,s); 3.49 (2H,t J=6.44); 2.53 (2H,t J=7.16) ; 2.20 (2H,m) .
70% for 16 h; Reflux; Inert atmosphere General procedure: Typical procedure: After refluxing the mixture of 4a (7.64g, 45.7mmol), methanol (78.4mL), and conc. sulfuric acid (0.77mL) for 16h under a dry argon atmosphere, it was cooled to room temperature. Then, aqueous solution of sodium bicarbonate (78mL) was added to the reaction mixture and the crude product was extracted with ethyl acetate. After washing the combined organic layer with sodium bicarbonate aqueous solution, water, and brine, it was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluted with a mixed solvent of chloroform/methanol (10/1v/v). The fraction with an Rf value of 0.86 was collected and dried under reduced pressure to afford methyl 4-bromobutanoate (5a) as yellow oil (5.82g, 70percent). (0016) 1H NMR (400MHz, CDCl3, ppm): δ 2.18 (quint, J=7.0Hz, 2H, BrCH2CH2), 2.52 (quint, J=7.1Hz, 2H, Br(CH2)2CH2), 3.47 (t, J=6.4Hz, 2H, BrCH2CH2), and 3.69 (s, 3H, OCH3). 13C NMR (100MHz, CDCl3, ppm): δ 27.70 (BrCH2CH2), 32.18 (Br(CH2)2CH2), 32.68 (BrCH2), 51.71 (OCH3), and 172.98 (COOCH3). IR (NaCl, cm−1): 1738 (C=O)
Reference: [1] Tetrahedron, 2014, vol. 70, # 44, p. 8343 - 8347
[2] Chemistry - An Asian Journal, 2011, vol. 6, # 1, p. 122 - 127
[3] Patent: WO2011/92065, 2011, A1, . Location in patent: Page/Page column 75-76
[4] Journal of Pharmacology and Experimental Therapeutics, 2016, vol. 357, # 2, p. 240 - 247
[5] Journal of the American Chemical Society, 2018, vol. 140, # 17, p. 5805 - 5813
[6] Heterocycles, 2017, vol. 94, # 8, p. 1518 - 1541
[7] Reactive and Functional Polymers, 2016, vol. 99, p. 1 - 8
[8] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1886, vol. 102, p. 369[9] Bulletin de la Societe Chimique de France, 1886, vol. <2>46, p. 65
[10] Tetrahedron, 2000, vol. 56, # 41, p. 8083 - 8094
[11] Journal of Organometallic Chemistry, 2009, vol. 694, # 3, p. 323 - 331
[12] Organic and Biomolecular Chemistry, 2009, vol. 7, # 9, p. 1821 - 1828
[13] Patent: WO2011/101245, 2011, A1, . Location in patent: Page/Page column 55
[14] Chemical Communications, 2012, vol. 48, # 46, p. 5793 - 5795
[15] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 6981 - 6995
[16] Journal of the American Chemical Society, 2017, vol. 139, # 44, p. 15576 - 15579
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YieldReaction ConditionsOperation in experiment
99% at 0 - 20℃; Inert atmosphere 4-Bromobutanoyl chloride (3.1 ml, 25.28 mmol) was added to 15 ml of dry metanol at 00C. Stirring was continued at 00C under Ar for 2 h then at RT overnight. The mixture was evaporated, diluted with EtAc/Hexane (1 :5), filtered through SiO2 gel, and evaporated to afford 4.50 g (99percent) of the title compound. . 1H NMR (CDCl3) 3.65 (s, 3H), 3.43 (t, 2H, J = 6.5 MHz), 2.47 (t, 2H, J = 7.1 MHz), 2.13 (dt, 2H, J = 6.7, 13.6 MHz); 13C NMR 173.08, 51.84, 32.82, 32.34, 27.89; MS m/z+ 203.0 (M + Na).
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 5, p. 1348 - 1355
[2] Patent: WO2010/91150, 2010, A1, . Location in patent: Page/Page column 153
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YieldReaction ConditionsOperation in experiment
83.4% at 0 - 25℃; for 72.5 h; 4-Bromobutanoic acid (7.5 g, 45.2 mmole) was dissolved in methanol (50 mL), and then CH3SiCl(11.4 mL, 90.4 mmole) was added at 0 °C; the mixture was stirred at this temperature for 30 min andfor 72 h at 25 °C. The solvent was removed in vacuuo. The resultant residue was purified by columnchromatography (silica-gel) eluting with hexanes:ethyl acetate 90:10 to afford the title compound as acolorless oil (6.78 g, 83.4percent). 1H-NMR (CDCl3): δ 3.68 (s, 3H), 3.46 (t, J = 6.4 Hz, 2H), 2.50 (t, J = 7.2 Hz,2H), 2.22–2.13 (m, 2H). 13C-NMR (CDCl3): δ173.11, 51.85, 32.80, 32.34, 27.87. HRMS (FAB+): m/z [M]+calcd for C5H9BrO2: 179.9786, found (M + 1): 180.9786.
Reference: [1] Molecules, 2018, vol. 23, # 11,
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Reference: [1] Angewandte Chemie - International Edition, 2001, vol. 40, # 19, p. 3672 - 3674
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 5790
[2] Patent: US2880220, 1956, ,
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Reference: [1] Journal of Organic Chemistry, 1969, vol. 34, p. 3332 - 3335
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Reference: [1] Helvetica Chimica Acta, 1982, vol. 65, # 4, p. 1197 - 1201
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Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 1, p. 3 - 10
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1966, vol. 34, p. 262 - 271
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Reference: [1] Journal of Organic Chemistry, 1951, vol. 16, p. 1417,1418
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Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7756 - 7767
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Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 13, p. 1793 - 1796
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Reference: [1] Canadian Journal of Chemistry, 1971, vol. 49, p. 1070 - 1084
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