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Chemistry
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3-Bromo-N-propylbenzamide
Chemistry
Organic Building Blocks
Aryls
Amines Bromides Amides Benzene Compounds

[ CAS No. 35306-74-2 ] {[proInfo.proName]}

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Chemical Structure| 35306-74-2
Chemical Structure| 35306-74-2
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Product Details of [ 35306-74-2 ]

CAS No. :35306-74-2 MDL No. :MFCD01215160
Formula : C10H12BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 242.11 Pubchem ID :-
Synonyms :

Safety of [ 35306-74-2 ]

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
GHS Pictogram:

Application In Synthesis of [ 35306-74-2 ]

* 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.

  • Downstream synthetic route of [ 35306-74-2 ]

[ 35306-74-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 107-10-8 ]
  • [ 1711-09-7 ]
  • [ 35306-74-2 ]
YieldReaction ConditionsOperation in experiment
67% With triethylamine In dichloromethane at -5 - 20℃; for 1h; 29.a Step a) 3-Bromo-N-propyl-benzamide A mixture of N-propyl amine (0.33 mL, 4.1 mmol) and triethylamine (0.83 mL, 5.8 mmol) in methylene chloride was cooled to -5° C., treated with 3-bromobenzoyl chloride (1 g, 4.5 mmol), warmed to room temperature, stirred at room temperature for 1 h, poured into aqueous sodium bicarbonate and extracted with methylene chloride. The extracts were combined, washed sequentially with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. The resultant residue was purified by flash chromatography on silica gel, 2:1 hexane/ethyl acetate as eluent, to give 3-bromo-N-propyl-benzamide as a white solid, 0.74 g (67% yield); 1H NMR (DMSO-d6) δ 0.8 (t, 3H); 1.5 (m, 2H); 3.2 (t, 2H); 7.4 (t, 1H); 7.6 (d, 1H), 7.8 (d, 1H); 7.9 (s, 1H); 8.5 (b, 1H); MS [(+)ESI] m/z 242[M-H]+.
With triethylamine In dichloromethane at 0 - 20℃; for 16h; 1.A Preparation Method 1:;Amides (1) were prepared by the method shown in Scheme 4. An appropriately substituted benzoic acid was refluxed in neat SOCk (150uL for 1 mmol of acid). The resulting acid chloride was dissolved in dichloromethane and treated at 0°C successively with triethylamine (1.2 equivalents) and an amine substituted with R3 (1.2 equivalents). The reaction was stirred at room temperature for 16 hours. The resulting amide was washed with 2M HC1, followed by saturated NaHCOs, then brine. The resulting solution was then dried over MgSO4.; 1A: N-n-propyl-3-bromobenzamideUsing Preparation Method 1,3-bromobenzoic acid was reacted with w-propylamine. The resulting reaction mixture was purified using SiO2 with CH2C12 (100%) to CH2Cl2/MeOH 99:1 to give N-ft-propyl-3-bromobenzamide as an off-white solid (79%). NMR 'H (ppm, CDC13): 7.86 (s, 1H), 7.63 (d, J* = 7.74 Hz, 1H), 7.50 (d, / - 7.00 Hz, 1H), 7.19-7.13 (m, 1H), 7.02 (br. s., 1H), 3.33-3.27 (m, 2H), 1.54 (sext, f = 7.34 Hz, 2H), 0.88 (t, J3 = 7.42 Hz, 3H).
3.8 g With triethylamine In dichloromethane at 0 - 20℃; for 16h;
Reference： [1]Current Patent Assignee: PFIZER INC - US2007/72925, 2007, A1 Location in patent: Page/Page column 33
[2]Current Patent Assignee: THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH - WO2006/2474, 2006, A1 Location in patent: Page/Page column 115; 119
[3]Brady, Ryan M.; Vom, Amelia; Roy, Michael J.; Toovey, Nathan; Smith, Brian J.; Moss, Rebecca M.; Hatzis, Effie; Huang, David C. S.; Parisot, John P.; Yang, Hong; Street, Ian P.; Colman, Peter M.; Czabotar, Peter E.; Baell, Jonathan B.; Lessene, Guillaume [Journal of Medicinal Chemistry, 2014, vol. 57, # 4, p. 1323 - 1343]
  • 2
  • [ 35306-74-2 ]
  • [ 98-80-6 ]
  • [ 620937-44-2 ]
YieldReaction ConditionsOperation in experiment
96% With sodium carbonate In ethanol; toluene at 80℃; 1.B Preparation Method 2;: Biphenyl compounds prepared by Suzuki couplingBiphenyl compounds at R3 and R4 may be introduced using Suzuki coupling between para-or meta-halogenated phenyl derivatives and substituted phenyl boronic acids. The two starting materials (1.1 equivalent of phenyl boronic acid) are dissolved in toluene (2.2 mL for 1 mmol of halogenated phenyl derivative). Ethanol (530 uL for 1 mmol of halogenated phenyl derivative), 2N Na2COs (1 mL for 1 mmol of halogenated phenyl derivative) and 5 mol% Pd(PPhs)4 were added successively to the starting mixture. The reaction was stirred at 80°C until the palladium precipitates. The resulting reaction mixture was dissolved with ethyl acetate and poured onto water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSC>4 and concentrated under vacuum.; IB: N-fl-propyl-3-phenylbenzamideUsing Preparation Method 2, N-n-propyl-3-bromobenzamide from Example 1A was reacted with phenyl boronic acid. The resulting reaction mixture was purified using SiO2 with CH2C12 (100%) to CH2Cl2/MeOH 90:10 to give N-n-propyl-3-phenylbenzamide as a white solid (96%). NMR .H (ppm, CDC13): 7.97 (t, / = 1.53 Hz, 1H), 7.69 (dd, f = 7.91 Hz, / = 1.84 Hz, 2H), 7.61-7.58 (m, 2H), 7.51-7.24 (m, 4H), 6.17 (br. s., 1H), 3.47-3.40 (m, 2H), 1.65 (sext., f = 7.32 Hz, 2H), 0.98 (t, f = 7.38 Hz, 3H).
96% With sodium carbonate In ethanol; water; toluene at 80℃; 1.1B Preparation Method 2: Biphenyl Compounds Prepared by Suzuki Coupling; Biphenyl compounds at R3 and R4 may be introduced using Suzuki coupling between para- or meta-halogenated phenyl derivatives and substituted phenyl boronic acids. The two starting materials (1.1 equivalent of phenyl boronic acid) are dissolved in toluene (2.2 mL for 1 mmol of halogenated phenyl derivative). Ethanol (530 μL for 1 mmol of halogenated phenyl derivative), 2N Na2CO3 (1 mL for 1 mmol of halogenated phenyl derivative) and 5 mol % Pd(PPh3)4 were added successively to the starting mixture. The reaction was stirred at 80° C. until the palladium precipitates. The resulting reaction mixture was dissolved with ethyl acetate and poured onto water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4 and concentrated under vacuum.; 1B: N-n-propyl-3-phenylbenzamide; Using Preparation Method 2, N-n-propyl-3-bromobenzamide from Example 1A was reacted with phenyl boronic acid. The resulting reaction mixture was purified using SiO2 with CH2Cl2 (100%) to CH2Cl2/MeOH 90:10 to give N-n-propyl-3-phenylbenzamide as a white solid (96%). NMR 1H (ppm, CDCl3): 7.97 (t, J4=1.53 Hz, 1H), 7.69 (dd, J3=7.91 Hz, J4=1.84 Hz, 2H), 7.61-7.58 (m, 2H), 7.51-7.24 (m, 4H), 6.17 (br. s., 1H), 3.47-3.40 (m, 2H), 1.65 (sext., J3=7.32 Hz, 2H), 0.98 (t, J3=7.38 Hz, 3H).
Reference： [1]Current Patent Assignee: THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH - WO2006/2474, 2006, A1 Location in patent: Page/Page column 115; 119
[2]Current Patent Assignee: THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH - US2008/153802, 2008, A1 Location in patent: Page/Page column 62; 64
  • 3
  • [ CAS Unavailable ]
  • [ 585-76-2 ]
  • [ 35306-74-2 ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: m-bromobenzoic acid With thionyl chloride Neat (no solvent); Heating / reflux; Stage #2: propylamine With triethylamine In dichloromethane at 0 - 20℃; for 16h; 1.1A Preparation Method 1:; Amides (1) were prepared by the method shown in Scheme 4. An appropriately substituted benzoic acid was refluxed in neat SOCl2 (150 μL for 1 mmol of acid). The resulting acid chloride was dissolved in dichloromethane and treated at 0° C. successively with triethylamine (1.2 equivalents) and an amine substituted with R3 (1.2 equivalents). The reaction was stirred at room temperature for 16 hours. The resulting amide was washed with 2M HCl, followed by saturated NaHCO3, then brine. The resulting solution was then dried over MgSO4.; 1A: N-n-propyl-3-bromobenzamide; Using Preparation Method 1,3-bromobenzoic acid was reacted with n-propylamine. The resulting reaction mixture was purified using SiO2 with CH2Cl2 (100%) to CH2Cl2/MeOH 99:1 to give N-n-propyl-3-bromobenzamide as an off-white solid (79%). NMR 1H (ppm, CDCl3): 7.86 (s, 1H), 7.63 (d, J3=7.74 Hz, 1H), 7.50 (d, J3=7.00 Hz, 1H), 7.19-7.13 (m, 1H), 7.02 (br. s., 1H), 3.33-3.27 (m, 2H), 1.54 (sext., J3=7.34 Hz, 2H), 0.88 (t, J3=7.42 Hz, 3H).
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;
Reference： [1]Current Patent Assignee: THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH - US2008/153802, 2008, A1 Location in patent: Page/Page column 62; 64
[2]Yoshimoto, Risa; Usuki, Yoshinosuke; Satoh, Tetsuya [Chemistry - An Asian Journal, 2020, vol. 15, # 6, p. 802 - 806]
  • 4
  • [ 381-98-6 ]
  • [ 35306-74-2 ]
  • C14H15BrF3NO3 [ No CAS ]
Reference： [1]Chemistry - An Asian Journal,2020

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