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[ CAS No. 31949-21-0 ]

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Chemical Structure| 31949-21-0
Chemical Structure| 31949-21-0
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CAS No. :31949-21-0 MDL No. :MFCD00000196
Formula : C9H9BrO2 Boiling Point : 323.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :229.07 g/mol Pubchem ID :123440
Synonyms :

Safety of [ 31949-21-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 31949-21-0 ]

  • Upstream synthesis route of [ 31949-21-0 ]
  • Downstream synthetic route of [ 31949-21-0 ]

[ 31949-21-0 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 579-74-8 ]
  • [ 31949-21-0 ]
YieldReaction ConditionsOperation in experiment
96% With copper(ll) bromide In chloroform; ethyl acetate at 70℃; for 8 h; Inert atmosphere; Reflux Copper (II) bromide (2.97 g, 6.66 mmol) was placed in a twonecked round-bottomed flask fitted with a reflux condenser. EtOAc (10.0 mL) was added to it and the mixture was stirred at 70C for 5 min under nitrogen atmosphere. 1-(2-Methoxyphenyl)ethanone (6) (0.50 g, 3.33 mmol) in CHCl3 (10.0 mL) was slowly added to it and then the mixture was refluxed for 8 h. After completion of the reaction, it was cooled to room temperature, filtered through Celite® pad, and washed with EtOAc (20 mL). The filtrate was concentrated under reduced pressure. The crude was puri- fied by column chromatography (EtOAc:hexane = 1:4) to afford the pure product 7a (0.73 g, 96percent) as brown liquid. Rf = 0.43 (EtOAc/hexane = 1/4); 1 H NMR (300 MHz, CDCl3): δ 7.81 (1H, dd, J = 7.8, 1.8 Hz), 7.52 (1H, td, J = 7.8, 1.8 Hz), 7.05–6.96 (2H, m), 4.61 (2H, s), 3.94 (3H, s); 13C NMR (75 MHz, CDCl3): δ 192.3, 158.8, 134.9, 131.6, 124.9, 121.2, 111.7, 56.0, 38.0.
83%
Stage #1: at 60℃;
Stage #2: at 60℃; for 0.25 h;
General procedure: The round-bottom flask containing acetophenone derivative 1, 10 (4 mmol) and PTSA (0.076 g,0.4 mmol) was heated to 60 °C to turn the reaction mixture into a paste and NBS (0.854 g, 4.8 mmol) thenadded slowly. After 15 min, the reaction mixture was cooled to room temperature and water (20 mL)added. The crude product was extracted with dichloromethane (2 x 20 mL), dried over anhydrousNa2SO4 and purified by crystallization from n-hexane–dichloromethane to give pure product. 2-Methoxyphenacyl bromide (2): Yellow solid, soluble in acetone, dichloromethane, chloroform, insolublein water; yield 83percent; m.p.: 43–45 °C; 1H-NMR (500 MHz, CDCl3) (δ, ppm): 7.78 (dd, 1H, J = 1.5,7.5 Hz, Ar–H), 7.51–7.47 (m, 1H, Ar–H), 7.02–6.96 (m, 2H, Ar–H), 4.57 (s, 2H, CH2), 3.93 (s, 3H, OCH3).This result showed consistency with the data in literature [26].
330 g With bromine In acetonitrile at 20 - 25℃; for 4 h; 1 -(2-methoxyphenyl)ethan-1 -one 2-bromo-1 - MW: 150.17 (2-methoxyphenyl)ethan-1-one MW: 229.07 [00242] l-(2-methoxyphenyl)ethanone, 1.1, (300 g, 1.0 eq) was added to a reactor containing acetonitrile (1.2 L, 4.0 V). Br2 (319.62 g, 1.0 eq) was added by cooling the reaction to below 25°C. The reaction mixture was stirred for 4 h at 20-25 °C and sampled for IPC until the content of l-(2-methoxyphenyl)ethanone was 6.5percent. NaHSCb (600 ml, 2V) was added to quench the reaction and then stirred for an additional 0.5h at 20-25°C. Product was extracted with methyl tert-butyl ether (600 ml, 2V), three times, to yield a black oil (418 g, crude), which was purified using a column to yield 330 g of 2-bromo-l-(2-methoxyphenyl)ethan-l-one, 1.2, as an off-white solid (98percent purity).
Reference: [1] Bulletin of the Korean Chemical Society, 2017, vol. 38, # 12, p. 1481 - 1485
[2] Tetrahedron Letters, 2006, vol. 47, # 27, p. 4707 - 4710
[3] Tetrahedron Letters, 2009, vol. 50, # 6, p. 700 - 703
[4] Chemistry - A European Journal, 2011, vol. 17, # 28, p. 7953 - 7959
[5] Molecules, 2017, vol. 22, # 5,
[6] Dalton Transactions, 2008, # 6, p. 822 - 831
[7] Journal of Medicinal Chemistry, 1987, vol. 30, # 8, p. 1497 - 1502
[8] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 5, p. 1170 - 1176
[9] Australian Journal of Chemistry, 1994, vol. 47, # 11, p. 2001 - 2012
[10] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 4, p. 719 - 722
[11] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1291 - 1295
[12] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1297 - 1303
[13] Tetrahedron, 2008, vol. 64, # 22, p. 5191 - 5199
[14] Chemistry - An Asian Journal, 2010, vol. 5, # 10, p. 2258 - 2265
[15] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 403 - 412
[16] Angewandte Chemie - International Edition, 2013, vol. 52, # 44, p. 11632 - 11636[17] Angew. Chem., 2013, vol. 125, # 44, p. 11846 - 11850,5
[18] Advanced Synthesis and Catalysis, 2013, vol. 355, # 18, p. 3570 - 3574
[19] Chemical Communications, 2014, vol. 50, # 51, p. 6726 - 6728
[20] Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6572 - 6582
[21] Journal of Materials Chemistry A, 2015, vol. 3, # 12, p. 6258 - 6264
[22] MedChemComm, 2015, vol. 6, # 6, p. 1036 - 1042
[23] European Journal of Medicinal Chemistry, 2015, vol. 104, p. 1 - 10
[24] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 8, p. 1166 - 1173
[25] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3669 - 3674
[26] Angewandte Chemie - International Edition, 2016, vol. 55, # 29, p. 8444 - 8447[27] Angew. Chem., 2016, vol. 128, # 29, p. 8584 - 8587,4
[28] Patent: KR101642378, 2016, B1, . Location in patent: Paragraph 0062-0066
[29] ChemMedChem, 2018, vol. 13, # 1, p. 37 - 47
[30] Patent: US2018/44459, 2018, A1, . Location in patent: Paragraph 0367
[31] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1986 - 1995
[32] Patent: US2018/44284, 2018, A1, . Location in patent: Paragraph 0175; 0176
[33] Organic Letters, 2018, vol. 20, # 8, p. 2257 - 2260
[34] Patent: WO2018/161008, 2018, A1, . Location in patent: Paragraph 00241-00242
[35] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 86, p. 12182 - 12185
  • 2
  • [ 4079-52-1 ]
  • [ 31949-21-0 ]
YieldReaction ConditionsOperation in experiment
31% With bromine In diethyl ether at 20℃; for 0.5 h; To a stirred solution of 2-methoxyacetophenone (10 g, 67 mmol) in diethyl ether (100 mL) was added dropwise bromine (10.6 g, 3.4 mL, 67 mmol) while the temperature was kept below 30 °C. The mixture was stirred at room temperature for 30 min, and then was evaporated to dryness to give the product,which was purified by distillation at 170 °C to give the product (4.77 g, 31percent) as colourless crystals; mp41–44 °C (lit.,34 40–44 °C); 1H NMR δ 7.84–7.81 (m, 1H, H-6), 7.55–7.49 (m, 1H, H-4), 7.06–6.98 (m,2H, H-3 and 5), 4.61 (s, 2H, CH2Br), 3.95 (s, 3H, OMe).
Reference: [1] Heterocycles, 2016, vol. 93, # 1, p. 164 - 184
  • 3
  • [ 1121543-12-1 ]
  • [ 31949-21-0 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 37, p. 4851 - 4855
  • 4
  • [ 118-93-4 ]
  • [ 31949-21-0 ]
Reference: [1] Chemistry - An Asian Journal, 2010, vol. 5, # 10, p. 2258 - 2265
[2] Journal of Materials Chemistry A, 2015, vol. 3, # 12, p. 6258 - 6264
  • 5
  • [ 1121543-12-1 ]
  • [ 123-54-6 ]
  • [ 5027-32-7 ]
  • [ 31949-21-0 ]
  • [ 1248587-21-4 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 37, p. 4851 - 4855
  • 6
  • [ 579-74-8 ]
  • [ 31949-21-0 ]
  • [ 1121543-12-1 ]
Reference: [1] Biochemistry, 2010, vol. 49, # 36, p. 7913 - 7919
  • 7
  • [ 31949-21-0 ]
  • [ 36449-75-9 ]
Reference: [1] Patent: WO2006/10379, 2006, A1, . Location in patent: Page/Page column 61
[2] Patent: WO2006/10544, 2006, A2, . Location in patent: Page/Page column 65
  • 8
  • [ 31949-21-0 ]
  • [ 27798-60-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 11, p. 2575 - 2582
  • 9
  • [ 31949-21-0 ]
  • [ 34589-97-4 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With hexamethylenetetramine In diethyl ether at 20℃; for 12 h;
Stage #2: With hydrogenchloride; water In ethanol for 3 h; Reflux
General procedure: To a stirred solution of 2-methoxyphenacyl bromide (7a)/phenacyl bromide (7b) (1 mmol, 1 equiv) in diethyl ether (13 mL) was added hexamethylenetetramine (1 mmol, 1 equiv) all at once and the mixture was stirred for 12 h at room temperature (solid formation observed). The resulting solid was filtered, washed with diethyl ether (15 mL), and dried under reduced pressure to afford the quaternary salt, which was next placed in a two-necked round-bottomed flask fitted with reflux condenser and EtOH (22 mL) was added to it. Concentrated HCl (0.6 mL) was added to it and the mixture was refluxed for 3 h (solid formed). After cooling to room temperature, the solid was filtered, washed with EtOH (20 mL), and dried under vacuum to afford pure 2- methoxybenzoylmethylammonium chloride (8a)/benzoylmethylammonium chloride (8b) salt. 2-Amino-1-(2-methoxyphenyl)ethanone hydrochloride (8a): Yield: 88percent; brown solid; mp 102–104C; 1 H NMR (300 MHz, CDCl3): δ 7.26 (1H, d, J = 8.7 Hz), 7.11 (1H, t, J = 7.2 Hz), 4.33 (2H, q, J = 5.4 Hz), 3.94 (3H, s); 13C NMR (75 MHz, CDCl3): δ 192.1, 159.6, 135.9, 130.0, 120.7, 112.9, 56.1, 48.7.
Reference: [1] Bulletin of the Korean Chemical Society, 2017, vol. 38, # 12, p. 1481 - 1485
[2] Patent: WO2008/145398, 2008, A1,
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