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[ CAS No. 22118-09-8 ]

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Product Details of [ 22118-09-8 ]

CAS No. :22118-09-8 MDL No. :MFCD00000724
Formula : C2H2BrClO Boiling Point : -
Linear Structure Formula :- InChI Key :SYZRZLUNWVNNNV-UHFFFAOYSA-N
M.W :157.39 Pubchem ID :89602
Synonyms :

Safety of [ 22118-09-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H314-H335 Packing Group:
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Application In Synthesis of [ 22118-09-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 22118-09-8 ]
  • Downstream synthetic route of [ 22118-09-8 ]

[ 22118-09-8 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 110-89-4 ]
  • [ 22118-09-8 ]
  • [ 1796-25-4 ]
  • [ 1440-60-4 ]
Reference: [1] Chemistry of Natural Compounds, 2013, vol. 48, # 6, p. 1047 - 1053[2] Khim. Prir. Soedin., 2012, vol. 48, # 6, p. 924 - 929,6
  • 2
  • [ 110-91-8 ]
  • [ 22118-09-8 ]
  • [ 1440-61-5 ]
Reference: [1] Chemistry of Natural Compounds, 2013, vol. 48, # 6, p. 1047 - 1053[2] Khim. Prir. Soedin., 2012, vol. 48, # 6, p. 924 - 929,6
  • 3
  • [ 67-56-1 ]
  • [ 22118-09-8 ]
  • [ 96-32-2 ]
Reference: [1] Journal of Molecular Structure, 1991, vol. 246, # 3/4, p. 267 - 278
  • 4
  • [ 22118-09-8 ]
  • [ 253185-03-4 ]
  • [ 30095-47-7 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 30, p. 4187 - 4196
  • 5
  • [ 22118-09-8 ]
  • [ 108-88-3 ]
  • [ 619-41-0 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 30, p. 4187 - 4196
  • 6
  • [ 22118-09-8 ]
  • [ 462-06-6 ]
  • [ 403-29-2 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 30, p. 4187 - 4196
  • 7
  • [ 22118-09-8 ]
  • [ 591-50-4 ]
  • [ 31827-94-8 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 30, p. 4187 - 4196
  • 8
  • [ 22118-09-8 ]
  • [ 683-57-8 ]
YieldReaction ConditionsOperation in experiment
73% With potassium carbonate In dichloromethane Step 1
To a solution of amine from Example 51 Step 1 (300 mg; 0.71 mmol) and potassium carbonate (290 mg; 2.1 mmol) in CH2Cl2 was added bromoacetyl chloride (71 l; 0.85 mmol) and the solution was stirred at room temperature overnight.
The reaction mixture was washed with 0.1 N aqueous NaOH, dried over Na2SO4, concentrated, and purified on a plug of silica gel (eluding CH2Cl2/AcOEt 9:1) to yield 281 mg (73percent) of bromoacetamide.
Reference: [1] Journal of the American Chemical Society, 1939, vol. 61, p. 3386
[2] Patent: US2003/216380, 2003, A1,
  • 9
  • [ 22118-09-8 ]
  • [ 124-40-3 ]
  • [ 5468-77-9 ]
YieldReaction ConditionsOperation in experiment
76% With triethylamine In acetonitrile at -78 - 20℃; for 2 h; Under an atmosphere of nitrogen, 2-bromoacetyl chloride (1.3 mL, 16 mmol) was added to a mixture of TEA (2.2 mL, 16 mmol) and dimethylamine (8 mL, 16 mmol) in MeCN (20 mL) at-78 °C. The stirred reaction mixture was then allowed to slowly warm to room temperature. After stirring for 2 hours, water was added (30 mL) and the mixture was extracted with DCM (3 x 40 mL). The combined organic layers were dried, and concentrated under vacuum to afford the desired product (2.03 g, 76percent) which was carried forward as crude material. MS (ESI): mass calcd. for C4H8BrNO, 166.1.1H NMR (500 MHz, DMSO-d6) δ 4.35 (s, 2H), 2.99 (s, 3H), 2.85 (s, 3H).
68.6% for 1 h; Preparation 98: 2-Bromo-N,N-dimethylacetamide; [00268] 2-Bromoacetic acid (1 g, 7.2mmol) was dissolved in dry dichloromethane (10ml). To the stirred solution was added oxalyl chloride (1 g, 7.92mmol) followed by DMF (1 drop) and the reaction was allowed to stir at room temperature for 1 hour. A solution of dimethylamine (5ml of a 2M solution in THF, 10 mmol) was added. After 1 hour, the reaction was concentrated in vacuo and applied to an SCX-2 column. The column was eluted with 30percent methanol in chloroform. The solvents were removed in vacuum and the crude product purified by silica gel column chromatography eluting with neat ethyl acetate to afford the title compound as a white powder (0.82g, 68.6percent).1 H-NMR (500 MHz, CDCI3): δ 2.97 (s, 3H), 3.1 (s, 3H), 3.86 (s, 2H).
Reference: [1] Patent: WO2018/67786, 2018, A1, . Location in patent: Page/Page column 104
[2] Patent: WO2012/123745, 2012, A1, . Location in patent: Page/Page column 95
  • 10
  • [ 22118-09-8 ]
  • [ 506-59-2 ]
  • [ 5468-77-9 ]
YieldReaction ConditionsOperation in experiment
38% With triethylamine In dichloromethane at 20℃; for 2 h; Preparation 40; 2-Bromo-Λ/.Λ/-dimethylacetanηide; Triethylamine (4.4mL, 33.3mmol) was added to a mixture of bromoacetyl chloride (1.05mL, 12.7mmol) and dimethylamine hydrochloride (1.25g, 15.2mmol) in dichloromethane and the mixture was stirred for 2 hours at room temperature. The mixture washed with 2M hydrochloric acid, 2M sodium hydroxide solution and brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound as a yellow oil in 38percent yield, 800mg. 1HNMR(400MHz, CDCI3) δ: 2.98(s, 3H), 3.09(s, 3H), 4.07(s, 2H); LRMS APCI m/z 168 [M+Hf
Reference: [1] Patent: WO2006/100588, 2006, A1, . Location in patent: Page/Page column 55
  • 11
  • [ 22118-09-8 ]
  • [ 75-31-0 ]
  • [ 75726-96-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 1, p. 20 - 24
[2] Journal of the American Chemical Society, 1993, vol. 115, # 20, p. 8898 - 8906
[3] Journal of the American Chemical Society, 1998, vol. 120, # 37, p. 9444 - 9451
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 6, p. 2482 - 2493
[5] Proceedings of the National Academy of Sciences of the United States of America, 2010, vol. 107, # 10, p. 4573 - 4578
  • 12
  • [ 22118-09-8 ]
  • [ 75-65-0 ]
  • [ 5292-43-3 ]
Reference: [1] Synthetic Communications, 1990, vol. 20, # 13, p. 2033 - 2040
[2] Chemische Berichte, 1986, vol. 119, # 4, p. 1196 - 1207
[3] Canadian Journal of Chemistry, 2003, vol. 81, # 8, p. 915 - 936
  • 13
  • [ 22118-09-8 ]
  • [ 91-16-7 ]
  • [ 1835-02-5 ]
Reference: [1] Farmaco, Edizione Scientifica, 1987, vol. 42, # 6, p. 465 - 473
  • 14
  • [ 22118-09-8 ]
  • [ 103-73-1 ]
  • [ 938-73-8 ]
  • [ 55836-71-0 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 30, p. 4187 - 4196
  • 15
  • [ 22118-09-8 ]
  • [ 108-67-8 ]
  • [ 4225-92-7 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 51, p. 12494 - 12501
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 30, p. 4187 - 4196
  • 16
  • [ 22118-09-8 ]
  • [ 98-16-8 ]
  • [ 25625-57-4 ]
YieldReaction ConditionsOperation in experiment
64% With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1 h; 3-Trifluoromethylaniline (1.6 g, 10 mmol) was dissolved in dichloromethane with DIEA (3.4 mL, 20 mmol), cooled to 0 °C, and to this solution bromoacetyl chloride was added as a neat liquid (exothermic). After 1 hour the reaction mixture was washed with IN HCl, dried and concentrated to a brown oil which was purified by column chromatography (10 to 40 percent EtOAc/liexanes) to give a light brown oil, 1.8 g, 6.4 mmol, 64percent YIELD. 1H NMR (500 MHz, CDC13) S 8. 19 (S, 1H), 7.75 (s, 1H), 7.68 (d, J = 8.1 Hz, 1H), 7.41 (t, J = 7.9 Hz, 1H), 7.35 (d, J = 7.8 HZ,, 3. 96 (s, 2H).
Reference: [1] Patent: WO2005/19190, 2005, A2, . Location in patent: Page/Page column 59
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 25, p. 7450 - 7465
[3] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 3, p. 1409 - 1419
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 3, p. 235 - 239
  • 17
  • [ 22118-09-8 ]
  • [ 455-14-1 ]
  • [ 3823-19-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 24, p. 10544 - 10550
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 1985 - 1988
[3] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 3, p. 235 - 239
  • 18
  • [ 22118-09-8 ]
  • [ 90-02-8 ]
  • [ 115787-50-3 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With aluminum (III) chloride In dichloromethane at 50℃; for 0.5 h;
Stage #2: at 40℃; for 12 h;
Anhydrous aluminum trichloride (20 g, 0.15 mol) was added to a 250 mL three-necked flask, and 15 mL of methylene chloride was added dropwise with stirring. The temperature was raised to 50 ° C, 10 mL of a methylene chloride solution of 7 g (0.045 mol) of bromoacetyl chloride was added dropwise and the mixture was stirred for 30 minutes. Salicylaldehyde (3.66 g, 0.03 mol) was dissolved in 10 mL of dichloromethane, dropped into the reaction mixture at 40 ° C. and refluxed for 12 hours. The reaction mixture was slowly poured into 120 g of crushed ice with stirring, the pH was adjusted to 4, and the mixture was stirred for 30 minutes. Then dichloromethane was added. The organic layer was separated and the aqueous layer was washed with dichloromethane (30 mL x 3). The organic phases were combined and the organic phase was washed with distilled water and brine successively, then dried over anhydrous magnesium sulfate, filtered, concentrated and dried in vacuo to give a purple oil. After stirring with 15 mL of dichloromethane, 60 mL of petroleum ether was added at 0 ° C to precipitate a light brown solid which was filtered and dried to give 6.1 g of 5-(bromoacetyl)salicylaldehyde in a yield of 84percent.
80% With aluminum (III) chloride In 1,2-dichloro-ethane at 70 - 80℃; for 36 h; (1) 250mL three-necked flask was added anhydrous aluminum chloride 200g (0.15mol)150 mL dichloroethane,The temperature was raised to 70 ° C,150 mL of a solution of 66.1 g (0.042 mol) of bromoacetyl chloride in dichloroethane was added dropwise,To be dissolved completely,Into the reaction liquid, 150 mL of dichloroethane of 36.6 g (0.03 mol) of salicylaldehyde was dropped at 70 ° C,After the dropwise addition, the temperature was raised to 80 ° C and reacted for 36 hours.The reaction solution was slowly poured into 1.0kg crushed ice with stirring,Add 100mL concentrated hydrochloric acid, the organic layer was separated,The aqueous layer was extracted with 200 mL of dichloroethane, the combined dichloroethane layers,Washed with water (300 mL × 2), washed with saturated brine (300 mL), dried over anhydrous sodium sulfate,Concentrated to give a yellow oil,Crystallization from petroleum ether-methylene chloride, filtration,Dried to give a white solid Intermediate III58g, yield 80percent;
Reference: [1] Patent: CN104557572, 2017, B, . Location in patent: Paragraph 0041; 0042; 0043; 0044
[2] Patent: CN104829468, 2017, B, . Location in patent: Paragraph 0040; 0041
[3] Synthetic Communications, 1999, vol. 29, # 12, p. 2155 - 2162
[4] Patent: WO2005/63777, 2005, A1, . Location in patent: Page/Page column 51
  • 19
  • [ 22118-09-8 ]
  • [ 90-02-8 ]
  • [ 115787-51-4 ]
  • [ 115787-50-3 ]
Reference: [1] Synthesis, 1988, # 12, p. 966 - 972
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