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Product Details of [ 20357-20-4 ]

CAS No. :20357-20-4 MDL No. :MFCD00456508
Formula : C7H4BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :UFRVBZVJVRHSNR-UHFFFAOYSA-N
M.W : 230.02 Pubchem ID :97233
Synonyms :

Calculated chemistry of [ 20357-20-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.35
TPSA : 62.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.2
Log Po/w (XLOGP3) : 2.49
Log Po/w (WLOGP) : 2.17
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 0.51
Consensus Log Po/w : 1.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.07
Solubility : 0.195 mg/ml ; 0.000846 mol/l
Class : Soluble
Log S (Ali) : -3.46
Solubility : 0.0805 mg/ml ; 0.00035 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.597 mg/ml ; 0.00259 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 20357-20-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20357-20-4 ]

* 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 [ 20357-20-4 ]
  • Downstream synthetic route of [ 20357-20-4 ]

[ 20357-20-4 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 20357-20-4 ]
  • [ 56904-86-0 ]
  • [ 1075-34-9 ]
YieldReaction ConditionsOperation in experiment
45% With triphenylphosphine In diphenylether at 260℃; for 1 h; General procedure: In a 50 ml round bottom flask containing magnetic stir bar was charged with o-nitro benzaldehydes (2 mmol), phosphorane (2.2 mmol), triphenyl phosphine (4.6 mmol) and diphenyl ether (10 mL) and heated at 260 oC for 1 h. The reaction mass was then cooled to room temperature and poured on silica column. Products were isolated by eluting with petrolium ether to 3:1 pet ether: ethyl acetate.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 19, p. 1851 - 1854
  • 2
  • [ 20357-20-4 ]
  • [ 74-89-5 ]
  • [ 465529-56-0 ]
Reference: [1] Patent: WO2016/14904, 2016, A1, . Location in patent: Page/Page column 21; 22
  • 3
  • [ 20357-20-4 ]
  • [ 39859-36-4 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 33, p. 9513 - 9515
  • 4
  • [ 552-89-6 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
YieldReaction ConditionsOperation in experiment
24% at 25℃; for 3 h; Treatment of 1 (986 mg, 6.53 mmol) with NBS (878 mg, 4.93 mmol) in H2SO4 (conc. 5.0 mL), as described in the paper gave after chromatography (hexanes/EtOAc, 8:2) the following fractions in order of elution: (I) 4-bromo-2-nitrobenzaldehyde (2)1 (216 mg, 19percent), 5-bromo-2-nitrobenzaldehyde (4)2 (134 mg, 12percent), and 4,5-dibromo-2-nitrobenzaldehyde (7) (18 mg, 1percent) as a yellow solid; (II) 6-bromo-2-nitrobenzaldehyde (5) (268 mg, 24percent),3 3,6-dibromo-2-nitrobenzaldehyde (8) (25 mg, 2percent),4 and 1 (409 mg, 41percent) as a yellow oil; (III) 3-bromo-2-nitrobenzaldehyde (3)5 as a yellow solid (60 mg, 0.26 mmol, 4percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 5
  • [ 552-89-6 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
  • [ 1559060-83-1 ]
YieldReaction ConditionsOperation in experiment
21% at 25℃; for 3 h; N-Bromosuccinimide (NBS) (1.48 g, 8.32 mmol) was added to a solution of 1 (1.01 g, 6.71 mmol) in H2SO4 (concentrated 5.0 mL). The resulting mixture was stirred at ambient temperature (3 h). The reaction was quenched with ice and extracted with ethyl acetate (320mL). The combined organic phases were washed with saturated NaCl (aqueous, 30 mL), dried (MgSO4), and filtered through a silica gel plug, and the solvents were evaporated under reduced pressure. The resulting brown oil was purified by column chromatography (hexanes=EtOAc, 8:2) to afford the following fractions in order of elution: (I) 7 (28 mg, 0.09 mmol, 1percent) as an off-white solid; (II) 2 (328 mg, 21percent), 4 (140 mg, 9percent), and 3,4-dibromo-2-nitrobenzaldehyde (6) (94 mg, 5percent); (III) 5 (310 mg, 20percent), 8 (65 mg, 3percent), 1 (168 mg, 17percent); (IV) 3 (54 mg, 0.23 mmol, 4percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 6
  • [ 552-89-6 ]
  • [ 882772-99-8 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
  • [ 1559060-83-1 ]
YieldReaction ConditionsOperation in experiment
20% at 25℃; for 3 h; Treatment of 1 (504 mg, 3.33 mmol) and NBS (1.48 g, 8.30 mmol) in H2SO4 (3.0 mL) as described above provided after purification by chromatography (hexanes/EtOAc, 85:15) the following fractions in order of elution: (I) 7 (65 mg, 0.21 mmol, 9percent); (II) 2 (153 mg, 20percent), 4 (58 mg, 8percent), and 6 (128 mg, 12percent); (III) 5 (108 mg, 14percent), 8 (129 mg, 13percent), and 1 (17 mg, 3percent); (IV) 3 (57 mg, 0.25 mmol, 8percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 7
  • [ 105205-48-9 ]
  • [ 20357-20-4 ]
YieldReaction ConditionsOperation in experiment
71% With sodium periodate In tetrahydrofuran; water at 20℃; for 1 h; Preparation of 5-bromo-2-nitro-benzaIdehyde (105):[0192] Compound 104 (11.63 g (42.9 mmol)) was dissolved in 500 mL 1 : 1 mixture of THF and water. To this solution 34.3 g (160 mmol) NaIO4 was added and the mixture was stirred at room temperature for 1 hr while the dark solution became pale yellow with a heavy precipitate. The solid material was filtered off, washed twice with 100 mL ethyl acetate and the organic phases were pooled and evaporated to dryness. The residue was filtered through a 400 mL silicagel pad using toluene for elution to get 7.08 g (71percent) of the title compound; H1-NMR (DMSO-d6): J (ppm) 10.10 (s, 1H), 8.09-7.99 (m, 3H).
71% With sodium periodate In tetrahydrofuran; water at 20℃; for 1 h; Compound 7.4 (11.63 g (42.9 mmol)) was dissolved in 500 mL 1:1 mixture of THF and water. To this solution 34.3 g (160 mmol) NaIO4 was added and the mixture was stirred at room temperature for 1 hr while the dark solution became pale yellow with a heavy precipitate. The solid material was filtered off, washed twice with 100 mL ethyl acetate and the organic phases were pooled and evaporated to dryness. The residue was filtered through a 400 mL silica gel pad using toluene for elution to get 7.08 g (71percent) of the title compound; H1-NMR (DMSO-d6): ?(ppm) 10.10 (s, 1H), 8.09-7.99 (m, 3H).
Reference: [1] Patent: WO2006/76529, 2006, A1, . Location in patent: Page/Page column 92; 93
[2] Patent: US2007/32488, 2007, A1, . Location in patent: Page/Page column 28-29
  • 8
  • [ 3132-99-8 ]
  • [ 20357-20-4 ]
YieldReaction ConditionsOperation in experiment
73.1% at 10℃; for 4 h; Under ice-water bath conditions,To a 1L round bottom flask 289ml three mass fraction of 98percent sulfuric acid (5.4mol),64 ml of Compound II (0.54 mol) was added dropwise slowly with stirring,Plus completed,After the temperature of the system dropped to 10 ° C, 27 ml of nitric acid (0.59 mol) in a mass ratio of 65percent was slowly added dropwise to the system,Plus complete TLC monitoring,The reaction was complete for 4 hours,The reaction was slowly poured into 2 L of ice water,Filtration,The filter cake was washed with water,Wash to the filtrate without acid,The solid was recrystallized from n-hexane and ethyl acetate to give 91 g of compound III as a white solid,Yield 73.1percent.
70% With sulfuric acid; nitric acid In water at 5 - 20℃; To concentrated nitric acid (10 mL) in concentrated sulfuric acid (120 mL) at 5°C was added 3- bromobenzaldehyde (11.7 mL, 100 mmol) dropwise. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured onto ice and the resulting precipitate removed by filtration, dissolved in dichloromethane, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 25percent ethyl acetate/isohexane, EPO <DP n="18"/>to give 5-bromo-2-nitrobenzaldehyde (16 g, 70percent). δH (500 MHz, CDCl3): 10.41 (1 H, s), 8.06 (1 H, d, J = 2.1 Hz), 8.02 (1 H, d, J = 8.6 Hz), 7.87 (1 H, dd, J = 2.1, 8.6 Hz).
68.4% at 20℃; for 6 h; Cooling with ice The concentrated sulfuric acid (70 mL) and 70percent concentrated nitric acid (5 mL) were mixed under ice-3-Bromobenzaldehyde (10 g, 54 mmol) was added.After 6 h reaction at room temperature,The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic phase was washed with saturated brine, dried and concentrated. The crude product was beaten (ethyl acetate / petroleum ether = 1/5, v / v) and dried to give 5-brom0-2-nitrobenzaldehyde (8.5 g) in a yield of 68.4percent.
64% With sulfuric acid; nitric acid In water at 0 - 20℃; for 5 h; 31a)
5-Bromo-2-nitro-benzaldehyde
3-Bromo-benzaldehyde (18.50 g, 99.99 mmol) was added to a stirred solution of concentrated nitric acid (70percent, 13.09 mL, 199.98 mmol) in concentrated sulfuric acid (125 mL) at 0° C.
After the addition was complete, the ice bath was removed and the reaction was allowed to stir for 5 hours at room temperature.
Then, the mixture was poured into ice and the solid was collected by filtration.
The filtrate was extracted with diethyl ether.
The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated.
The residue was combined with the solid previously obtained via the first filtration and dissolved in diethyl ether.
56% at 0℃; for 0.75 h; 10049] Therefore an alternative approach was adopted in which benzaldehyde 11 was nitrated to the known benzaldehyde 12, which in turn was subjected to reductive amination by condensing it with ammonium hydroxide, using sodium borohydride as reducing agent to produce amine 13 in high yield. Acetylation amine 13 generated acetamide 14, which was reacted with tert-butyl piperazine- 1 -carboxylate under l3uchwald-Hartwig conditions to afford intermediate 15 in good yield. Reduction of nitro group of 15 over Pd——C in a Parr apparatus produced intermediate 16 in 91percent yield high yield. Exposure of intermediate 16 under basic conditions rendered the desired diamine 17 in good yield after colunm purifications. Reaction of 17 with CDI in THF, heating the mixture at 80° C. for 6 hours, gave access to the key intermediate 10 in an overall yield of 33percent from 14. Exposure of intermediate 10 to trifluoroacetic acid in a mixture of methanol and dichloromethane finally thrnished the desired key intermediate 18 (scheme 2).
54% at 25℃; Step A: Potassium nitrate (49.2 g, 0.486 mol) was added to 240 g of cooled sulfuric acid in a three neck round bottom flask, keeping the temperature below 25 °C. This was followed by the slow addition of 3-bromobenzaldehyde (30.0 g, 0.162 mol). Once the addition was complete, the mixture was allowed to gradually warm to room temperature overnight. The mixture was then poured into 500 mLs of ice water, resulting in a light yellow precipitate. The solids were collected by filtration and dried under vacuum for several hours. Purification of the crude product was done in the following way: The collected solids were divided into two lots and each lot purified using two 340 g Biotage Snap Cartridges in series with 3: 1 Hexanes:EtOAc as the eluant. Obtained 20 g of 5-bromo-2-nitrobenzaldehyde (54percent) as a light yellow solid. NMR (400 MHz, CDC13) δ 10.42 (s, 1H), 8.07, (d, 1H), 8.03, (d, 1H), 7.89 (dd, 1H).
48% for 0.416667 h; cooling with ice Step a: To an ice cold cone, sulphuric acid (400 mL) was added fuming nitric acid (200 mL) and to this solution was added 3-bromobenzaldehyde (i) (100 g, 0.540 mol) dropwise within 15 min. The reaction mixture was stirred for 10 min at same temperature at which time TLC showed complete reaction. The reaction mixture was quenched in ice water and filtered to afford a mixture of products which was purified by flash column chromatography eluting with EtOAc/hexane (1-5 percent) to give 5-bromo-2-nitrobenzaldehyde (ii) as white solid (60 g, 48 percent).
48% Cooling with ice 5-Bromo-2-nitrobenzaldehyde (ii) To ice cold conc. sulphuric acid (400 mL) was added fuming nitric acid (200 mL) dropwise followed by 3-bromobenzaldehyde (i) (100 g, 0.540 mol) dropwise over 15 min.
The reaction mixture was stirred for 10 min and then poured carefully over ice-water.
The resulting solids were filtered and then purified by flash column chromatography on silica gel, eluting with EtOAc:n-hexane (gradient elution from 1percent to 20percent v/v) to give (ii) (60 g, 48percent).
48% at 0℃; for 0.416667 h; Fuming nitric acid (200 mL) was added to sulphuric acid (400 mL) at 0 °C and then 3- bromobenzaldehyde (100 g, 0.54 mol) was added dropwise in 15 minutes. After stirring for 10minutes at the same temperature, the reaction mixture was poured into ice water and filtered to afford the mixture of products which was purified by flash column chromatography eluting with PE / EtOAc (100 / 1 to 20 / 1) to give 5-bromo-2-nitrobenzaldehyde as white solid (60 g, 48 percent). ‘H-NMR (CDC13, 400 MHz) 10.41 (s, 1H), 8.028.06 (m, 2H), 7.88 (s, 1H). MS (M+H): 230 /232.
48% at 0℃; for 0.416667 h; Fuming nitric acid (200 mL) was added to sulphuric acid (400 mL) at 0 °C and then 3-bromobenzaldehyde (100 g, 0.54 mol) was added dropwise in 15 minutes. After stirring for 1010 minutes at the same temperature, the reaction mixture was poured into ice water and filtered toafford the mixture of products which was purified by flash column chromatography eluting withPE I EtOAc (100 I 1 to 20 I 1) to give 5-bromo-2-nitrobenzaldehyde as white solid (60 g, 48 percent).1H-NMR (CDCh, 400 MHz) 8 10.41 (s, 1H), 8.02~8.06 (m, 2H), 7.88 (s, 1H). MS (M+Ht: 230I 232.

Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 7, p. 2442 - 2449
[2] Patent: CN105669566, 2016, A, . Location in patent: Paragraph 0027; 0028; 0029; 0030; 0031
[3] Journal of Organic Chemistry, 2014, vol. 79, # 17, p. 7822 - 7830
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 33, p. 6115 - 6122
[5] Patent: WO2006/100519, 2006, A1, . Location in patent: Page/Page column 16-17
[6] Patent: CN106349241, 2017, A, . Location in patent: Paragraph 0406; 0407; 0408; 0409
[7] Molecules, 2012, vol. 17, # 5, p. 5497 - 5507
[8] Patent: US2008/96921, 2008, A1, . Location in patent: Page/Page column 78
[9] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 2031 - 2036
[10] Patent: US2015/232448, 2015, A1, . Location in patent: Paragraph 0049
[11] Patent: WO2012/97177, 2012, A2, . Location in patent: Page/Page column 43-44
[12] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3488 - 3491
[13] Chemistry - A European Journal, 2011, vol. 17, # 10, p. 2981 - 2986
[14] Patent: WO2012/51659, 2012, A1, . Location in patent: Page/Page column 53
[15] Patent: US2013/274179, 2013, A1, . Location in patent: Paragraph 0261
[16] Patent: WO2014/123793, 2014, A1, . Location in patent: Page/Page column 85
[17] Patent: WO2014/121416, 2014, A1, . Location in patent: Page/Page column 85
[18] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7492 - 7502
[19] Organic Letters, 2003, vol. 5, # 13, p. 2251 - 2253
[20] Chemische Berichte, 1905, vol. 38, p. 2812
[21] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 147
[22] Justus Liebigs Annalen der Chemie, 1895, vol. 284, p. 145
[23] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 147
[24] Justus Liebigs Annalen der Chemie, 1895, vol. 284, p. 145
[25] Chemische Berichte, 1905, vol. 38, p. 2812
[26] Synthesis, 2006, # 15, p. 2475 - 2477
[27] Patent: WO2009/97401, 2009, A1, . Location in patent: Page/Page column 51
[28] Organic and Biomolecular Chemistry, 2008, vol. 6, # 18, p. 3284 - 3291
[29] Patent: US2007/232630, 2007, A1, . Location in patent: Page/Page column 25
[30] European Journal of Organic Chemistry, 2014, vol. 2014, # 26, p. 5827 - 5835,9
[31] Tetrahedron Letters, 2016, vol. 57, # 8, p. 959 - 963
[32] Patent: CN103467300, 2016, B,
[33] Patent: CN106943602, 2017, A, . Location in patent: Paragraph 0050; 0052; 0053
[34] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 146
[35] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 146
  • 9
  • [ 552-89-6 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
YieldReaction ConditionsOperation in experiment
24% at 25℃; for 3 h; Treatment of 1 (986 mg, 6.53 mmol) with NBS (878 mg, 4.93 mmol) in H2SO4 (conc. 5.0 mL), as described in the paper gave after chromatography (hexanes/EtOAc, 8:2) the following fractions in order of elution: (I) 4-bromo-2-nitrobenzaldehyde (2)1 (216 mg, 19percent), 5-bromo-2-nitrobenzaldehyde (4)2 (134 mg, 12percent), and 4,5-dibromo-2-nitrobenzaldehyde (7) (18 mg, 1percent) as a yellow solid; (II) 6-bromo-2-nitrobenzaldehyde (5) (268 mg, 24percent),3 3,6-dibromo-2-nitrobenzaldehyde (8) (25 mg, 2percent),4 and 1 (409 mg, 41percent) as a yellow oil; (III) 3-bromo-2-nitrobenzaldehyde (3)5 as a yellow solid (60 mg, 0.26 mmol, 4percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 10
  • [ 552-89-6 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
  • [ 1559060-83-1 ]
YieldReaction ConditionsOperation in experiment
21% at 25℃; for 3 h; N-Bromosuccinimide (NBS) (1.48 g, 8.32 mmol) was added to a solution of 1 (1.01 g, 6.71 mmol) in H2SO4 (concentrated 5.0 mL). The resulting mixture was stirred at ambient temperature (3 h). The reaction was quenched with ice and extracted with ethyl acetate (320mL). The combined organic phases were washed with saturated NaCl (aqueous, 30 mL), dried (MgSO4), and filtered through a silica gel plug, and the solvents were evaporated under reduced pressure. The resulting brown oil was purified by column chromatography (hexanes=EtOAc, 8:2) to afford the following fractions in order of elution: (I) 7 (28 mg, 0.09 mmol, 1percent) as an off-white solid; (II) 2 (328 mg, 21percent), 4 (140 mg, 9percent), and 3,4-dibromo-2-nitrobenzaldehyde (6) (94 mg, 5percent); (III) 5 (310 mg, 20percent), 8 (65 mg, 3percent), 1 (168 mg, 17percent); (IV) 3 (54 mg, 0.23 mmol, 4percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 11
  • [ 552-89-6 ]
  • [ 882772-99-8 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
  • [ 1559060-83-1 ]
YieldReaction ConditionsOperation in experiment
20% at 25℃; for 3 h; Treatment of 1 (504 mg, 3.33 mmol) and NBS (1.48 g, 8.30 mmol) in H2SO4 (3.0 mL) as described above provided after purification by chromatography (hexanes/EtOAc, 85:15) the following fractions in order of elution: (I) 7 (65 mg, 0.21 mmol, 9percent); (II) 2 (153 mg, 20percent), 4 (58 mg, 8percent), and 6 (128 mg, 12percent); (III) 5 (108 mg, 14percent), 8 (129 mg, 13percent), and 1 (17 mg, 3percent); (IV) 3 (57 mg, 0.25 mmol, 8percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 12
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Reference: [1] Synthesis, 2008, # 14 SPEC. ISS., p. 2199 - 2210
  • 13
  • [ 51686-78-3 ]
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  • [ 20357-20-4 ]
Reference: [1] Chemische Berichte, 1989, vol. 122, p. 1199 - 1202
  • 14
  • [ 552-89-6 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
YieldReaction ConditionsOperation in experiment
24% at 25℃; for 3 h; Treatment of 1 (986 mg, 6.53 mmol) with NBS (878 mg, 4.93 mmol) in H2SO4 (conc. 5.0 mL), as described in the paper gave after chromatography (hexanes/EtOAc, 8:2) the following fractions in order of elution: (I) 4-bromo-2-nitrobenzaldehyde (2)1 (216 mg, 19percent), 5-bromo-2-nitrobenzaldehyde (4)2 (134 mg, 12percent), and 4,5-dibromo-2-nitrobenzaldehyde (7) (18 mg, 1percent) as a yellow solid; (II) 6-bromo-2-nitrobenzaldehyde (5) (268 mg, 24percent),3 3,6-dibromo-2-nitrobenzaldehyde (8) (25 mg, 2percent),4 and 1 (409 mg, 41percent) as a yellow oil; (III) 3-bromo-2-nitrobenzaldehyde (3)5 as a yellow solid (60 mg, 0.26 mmol, 4percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 15
  • [ 552-89-6 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
  • [ 1559060-83-1 ]
YieldReaction ConditionsOperation in experiment
21% at 25℃; for 3 h; N-Bromosuccinimide (NBS) (1.48 g, 8.32 mmol) was added to a solution of 1 (1.01 g, 6.71 mmol) in H2SO4 (concentrated 5.0 mL). The resulting mixture was stirred at ambient temperature (3 h). The reaction was quenched with ice and extracted with ethyl acetate (320mL). The combined organic phases were washed with saturated NaCl (aqueous, 30 mL), dried (MgSO4), and filtered through a silica gel plug, and the solvents were evaporated under reduced pressure. The resulting brown oil was purified by column chromatography (hexanes=EtOAc, 8:2) to afford the following fractions in order of elution: (I) 7 (28 mg, 0.09 mmol, 1percent) as an off-white solid; (II) 2 (328 mg, 21percent), 4 (140 mg, 9percent), and 3,4-dibromo-2-nitrobenzaldehyde (6) (94 mg, 5percent); (III) 5 (310 mg, 20percent), 8 (65 mg, 3percent), 1 (168 mg, 17percent); (IV) 3 (54 mg, 0.23 mmol, 4percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
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  • [ 552-89-6 ]
  • [ 882772-99-8 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
  • [ 1559060-83-1 ]
YieldReaction ConditionsOperation in experiment
20% at 25℃; for 3 h; Treatment of 1 (504 mg, 3.33 mmol) and NBS (1.48 g, 8.30 mmol) in H2SO4 (3.0 mL) as described above provided after purification by chromatography (hexanes/EtOAc, 85:15) the following fractions in order of elution: (I) 7 (65 mg, 0.21 mmol, 9percent); (II) 2 (153 mg, 20percent), 4 (58 mg, 8percent), and 6 (128 mg, 12percent); (III) 5 (108 mg, 14percent), 8 (129 mg, 13percent), and 1 (17 mg, 3percent); (IV) 3 (57 mg, 0.25 mmol, 8percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 17
  • [ 20357-20-4 ]
  • [ 29124-57-0 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; iron In ethanol; water at 80℃; for 4 h; 90 g of compound III (0.39 mmol) was added to a 1 L round bottom flask,To the system was added 300 ml of absolute ethanol,32 g of reduced iron powder (0.58 mol) was added under stirring,To the system was added 200 ml of 0.1 M HCl,Oil bath was heated to 80 ,The reaction was carried out for 4 hours,The substrate reaction was complete,A portion of the ethanol was removed by rotary evaporation,Solid precipitation,Filtration,The solid was slurried with methylene chloride to obtain 71 g of a pale yellow powder of Compound III,Yield 92percent.HPLC analysis showed a purity of 97percent No further purification was required for the next reaction.
Reference: [1] Synthesis, 2008, # 14 SPEC. ISS., p. 2199 - 2210
[2] Patent: CN105669566, 2016, A, . Location in patent: Paragraph 0032; 0033; 0034; 0035
[3] Organic Letters, 2003, vol. 5, # 13, p. 2251 - 2253
[4] Chemical Communications, 2011, vol. 47, # 33, p. 9513 - 9515
[5] Patent: WO2017/166104, 2017, A1, . Location in patent: Page/Page column 166
[6] Molecules, 2018, vol. 23, # 2,
  • 18
  • [ 20357-20-4 ]
  • [ 190273-89-3 ]
Reference: [1] Patent: CN105669566, 2016, A,
  • 19
  • [ 10601-80-6 ]
  • [ 20357-20-4 ]
  • [ 481054-89-1 ]
YieldReaction ConditionsOperation in experiment
60% With tin(II) chloride dihdyrate In ethanol at 20 - 90℃; Step 1:
ethyl 6-bromoquinoline-3-carboxylate
To a solution of 5-bromo-2-nitrobenzaldehyde (2 g, 9 mmol) in ethanol (46 mL) was added tin(II) chloride dihydrate (7.95 g, 35.2 mmol) and 3,3-diethoxypropionic acid ethyl ester (4.2 mL, 22 mmol).
The reaction was heated to 90° C. for 16 hours.
The reaction was then allowed to cool to room temperature and stir overnight.
The reaction mixture was concentrated and the residue was dissolved in ethyl acetate.
The mixture was poured into saturated aqueous sodium bicarbonate.
The resulting emulsion was filtered through Celite, rinsing with ethyl acetate.
The layers were separated and the aqueous was extracted with ethyl acetate.
The combined organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated.
Purification by flash column chromatography (0-50percent ethyl acetate/heptanes) gave the title compound (1.41 g, 60percent) as a solid.
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3488 - 3491
[2] Patent: US2012/270893, 2012, A1, . Location in patent: Page/Page column 32
  • 20
  • [ 552-89-6 ]
  • [ 882772-99-8 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
  • [ 1559060-83-1 ]
YieldReaction ConditionsOperation in experiment
20% at 25℃; for 3 h; Treatment of 1 (504 mg, 3.33 mmol) and NBS (1.48 g, 8.30 mmol) in H2SO4 (3.0 mL) as described above provided after purification by chromatography (hexanes/EtOAc, 85:15) the following fractions in order of elution: (I) 7 (65 mg, 0.21 mmol, 9percent); (II) 2 (153 mg, 20percent), 4 (58 mg, 8percent), and 6 (128 mg, 12percent); (III) 5 (108 mg, 14percent), 8 (129 mg, 13percent), and 1 (17 mg, 3percent); (IV) 3 (57 mg, 0.25 mmol, 8percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 21
  • [ 3132-99-8 ]
  • [ 882772-99-8 ]
  • [ 20357-20-4 ]
Reference: [1] Synthesis, 2008, # 14 SPEC. ISS., p. 2199 - 2210
  • 22
  • [ 20357-20-4 ]
  • [ 1241894-37-0 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 2 h; Cooling with ice (1) Take 20mL of concentrated nitric acid, stirred in an ice bath to 0 ° C, pipette 25mL of concentrated sulfuric acid, 20min stirring in an ice bath, then add 10g m-bromobenzaldehyde. Stir at room temperature for 4 h, add a small amount of water and adjust pH to 3-4 with NaOH. Then extracted three times with ethyl acetate, the organic phase was concentrated by evaporation to give the product 1; the product 1 was dissolved in 25mL of methanol, 2g of sodium borohydride was added in portions under ice bath and stirred at room temperature for 2h. The reaction mixture was added 20mL of water, then extracted with 20mL of ethyl acetate three times, the organic phase combined, dried over anhydrous sodium sulfate and concentrated by evaporation. The crude product was purified by column to afford 11.29g of product 2 in 90percent yield;
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 17, p. 7822 - 7830
[2] Patent: CN106943602, 2017, A, . Location in patent: Paragraph 0050; 0052; 0053
[3] Tetrahedron Letters, 2016, vol. 57, # 8, p. 959 - 963
  • 23
  • [ 102-52-3 ]
  • [ 20357-20-4 ]
  • [ 1196155-68-6 ]
Reference: [1] Patent: WO2011/63233, 2011, A1, . Location in patent: Page/Page column 32
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