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Chemical Structure| 20357-21-5
Chemical Structure| 20357-21-5
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Product Details of [ 20357-21-5 ]

CAS No. :20357-21-5 MDL No. :MFCD09040530
Formula : C7H4BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :WRIAMYXQKSDDRP-UHFFFAOYSA-N
M.W : 230.02 Pubchem ID :15063174
Synonyms :

Calculated chemistry of [ 20357-21-5 ]

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) : -7.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.06
Log Po/w (XLOGP3) : 0.87
Log Po/w (WLOGP) : 2.17
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 0.51
Consensus Log Po/w : 1.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.05
Solubility : 2.04 mg/ml ; 0.00887 mol/l
Class : Soluble
Log S (Ali) : -1.77
Solubility : 3.86 mg/ml ; 0.0168 mol/l
Class : Very 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 : 1.89

Safety of [ 20357-21-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20357-21-5 ]

* 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 [ 20357-21-5 ]
  • Downstream synthetic route of [ 20357-21-5 ]

[ 20357-21-5 ] Synthesis Path-Upstream   1~25

  • 1
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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
  • 2
  • [ 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
  • 3
  • [ 552-89-6 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-21-5 ]
  • [ 1559060-83-1 ]
YieldReaction ConditionsOperation in experiment
10% at 60℃; for 3 h; Treatment of 1 (459 mg, 3.03 mmol) and NBS (677 mg, 3.80 mmol) in H2SO4 (3.0 mL) at 60 oC as described above afforded the following fractions in order of elution: (I) 7 (21 mg, 0.07 mmol, 2percent); (II) 2 (66 mg, 9percent) and 4 (24 mg, 3percent); (III): 2 (5 mg, 0.7percent) and 3,4-dibromo-2-nitrobenzaldehyde 6 (85 mg, 9percent); (IV) 5 (59 mg, 8percent), 8 (13 mg, 1percent), and 1 (18 mg, 4percent); (V) 3 (20 mg, 0.09 mmol, 3percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 4
  • [ 552-89-6 ]
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  • [ 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
  • 5
  • [ 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
  • 6
  • [ 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
  • 7
  • [ 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
  • 8
  • [ 55289-35-5 ]
  • [ 20357-21-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2006, vol. 45, # 40, p. 6737 - 6741
[2] Journal of the American Chemical Society, 2007, vol. 129, # 29, p. 9109 - 9116
[3] Journal of the American Chemical Society, 2003, vol. 125, # 8, p. 2084 - 2093
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 6, p. 1565 - 1569
[5] Bulletin de la Societe Chimique de France, 1917, vol. <4> 21, p. 111
  • 9
  • [ 55289-35-5 ]
  • [ 4637-24-5 ]
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YieldReaction ConditionsOperation in experiment
67%
Stage #1: at 135℃; for 16 h;
Stage #2: With sodium periodate In water; N,N-dimethyl-formamide at 0 - 20℃; for 22 h;
Example 35; This example describes the synthesis of Aldehyde 10: To a stirred solution of 9 (4.94 g, 22.3 mmol) and DMF (22.3 mL) was added DMF'DMA (8.18 g, 9.59 mL, 68.6 mmol). After heating at 135°C for 16 h, the dark red solution was cooled to 0°C and added to a rapidly stirred solution OfNaIO4 (14.7 g, 68.6 mmol) in H2O (46 mL) and DMF (23 mL) at 0°C. The reaction flask was washed with DMF (23 mL) at 0°C and added to NaIO4 mixture. The reaction was stirred at O0C for 4 h then allowed to warm to rt. After an additional 18 h, the orange solution was filtered over a pad of celite-.(R). and rinsed with EtOAc (200 mL) to remove precipitate. The filtrate was then washed with H2O (3 x 150 mL) and sat. aq. NaCl (3 x 150 mL). The dried extract (MgSO4) was concentrated in vacuo and purified by chromatography over silica gel, eluting with 40percent EtOAc / Hexanes to give the known aldehyde 10 (3.44 g, 14.8 mmol, 67percent). 1H NMR (400 MHz, CDCl3) δ 10.3 (s, IH), 8.04 (dd, J= 1.0, 8.2 Hz, IH), 7.95 (dd, J= 1.0, 8.0 Hz, IH), 7.55 (t, J= 8.0 Hz, IH); 13C NMR (100 MHz, CDCl3) δ 188.6, 148.4, 138.6, 132.9, 132.4, 123.4, 121.9.
Reference: [1] Patent: WO2008/156656, 2008, A2, . Location in patent: Page/Page column 58; 66; 120
  • 10
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YieldReaction ConditionsOperation in experiment
92%
Stage #1: for 0.166667 h; Cooling; Green chemistry
Stage #2: at 45℃; for 0.833333 h; Irradiation; Green chemistry
The compound (II) o-nitrobenzaldehyde (0.80 g, 5.30 mmol) and concentrated sulfuric acid (98 wtpercent, 6.4 ml) were placed in a reaction flask and stirred under a cold well for 10 minutes.Then, NBS (1.13 g, 6.36 mmol) was slowly added and stirred for 5 minutes, and finally transferred to an oil bath at 45 ° C and allowed to react under light for 45 minutes.After the reaction was completed, it was cooled to room temperature, and the reaction mixture was poured into crushed ice and quenched, and then extracted with ethyl acetate (50 ml).Wash with saturated aqueous sodium hydrogencarbonate (50 ml), dry over anhydrous sodiumdry,Obtained 281 mg of bromo o-nitrobenzaldehyde (III) as a brownish yellow solid, yield 92.0percent, purity ≥98percent.
Reference: [1] Patent: CN108484623, 2018, A, . Location in patent: Paragraph 0047; 0048; 0049
  • 11
  • [ 397322-46-2 ]
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YieldReaction ConditionsOperation in experiment
26% With N-Bromosuccinimide; NaH In tetrahydrofuran; tetrachloromethane; water; toluene (28-6)
To a solution of the compound of Example 28-5 (194 mg) in carbon tetrachloride (5.0 mL) were added N-bromosuccinimide (156 mg) and 2,2'-azobis(isobutyronitrile) (16.3 mg) under nitrogen atmosphere, and the mixture was heated under reflux for 2 hours.
The reaction solution was cooled to room temperature, and the insoluble materials were removed by filtration.
The solvent was evaporated under reduced pressure to about 3 ml.
Further, toluene was added thereto, and the mixture was evaporated under reduced pressure to about 3 mL.
This procedure was repeated five times to give a solution of a crude bromo compound in toluene.
Under nitrogen atmosphere, a solution of the compound of Reference Example 1 (158 mg) in THF (5.0 mL) was cooled to 0°C, and thereto was added 60 percent NaH (37.06 mg).
Further, thereto was added the solution of the crude bromo compound in toluene, and the mixture was stirred at 50°C for 2 hours.
The reaction solution was cooled to room temperature, and water was added to the mixture, and further extracted twice with ethyl acetate.
The extract was washed with water and a saturated brine, dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure.
The residue was purified by silica gel column (hexane / ethyl acetate =3/ 1 --> 1/1) to give the title compound (90.9 mg, 26 percent).
1H NMR (CDCl3, 400MHz) δ 8.79 (d, 1H, J=2.1Hz), 8.20 (d, 1H, J=2.1Hz), 8.04 (d, 1H, J=8.4Hz), 7.80 (d, 1H, J=7.5Hz), 7.70 (d, 2H, J=8.0Hz), 7.53 (dd, 1H, J=7.5, 8.4Hz), 7.23 (d, 2H, J=8.0Hz), 7.11 (dd, 1H, J=1.7, 2.5Hz), 6.86 (dd, 1H, J=1.7, 4.0Hz), 6.31 (dd, 1H, J=2.5, 4.0Hz), 5.91 (s, 2H), 2.41 (s, 3H).
Reference: [1] Patent: EP1479384, 2004, A1,
  • 12
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YieldReaction ConditionsOperation in experiment
26% With N-Bromosuccinimide; NaH In tetrahydrofuran; tetrachloromethane; water; toluene (28-6)
To a solution of the compound of Example 28-5 (194 mg) in carbon tetrachloride (5.0 mL) were added N-bromosuccinimide (156 mg) and 2,2'-azobis(isobutyronitrile) (16.3 mg) under nitrogen atmosphere, and the mixture was heated under reflux for 2 hours.
The reaction solution was cooled to room temperature, and the insoluble materials were removed by filtration.
The solvent was evaporated under reduced pressure to about 3 ml.
Further, toluene was added thereto, and the mixture was evaporated under reduced pressure to about 3 mL.
This procedure was repeated five times to give a solution of a crude bromo compound in toluene.
Under nitrogen atmosphere, a solution of the compound of Reference Example 1 (158 mg) in THF (5.0 mL) was cooled to 0° C., and thereto was added 60percent NaH (37.06 mg).
Further, thereto was added the solution of the crude bromo compound in toluene, and the mixture was stirred at 50° C. for 2 hours.
The reaction solution was cooled to room temperature, and water was added to the mixture, and further extracted twice with ethyl acetate.
The extract was washed with water and a saturated brine, dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure.
The residue was purified by silica gel column (hexane/ethyl acetate=3/1-->1/1) to give the title compound (90.9 mg, 26percent).
1H NMR (CDCl3, 400 MHz) δ 8.79 (d, 1H, J=2.1 Hz), 8.20 (d, 1H, J=2.1 Hz), 8.04 (d, 1H, J=8.4 Hz), 7.80 (d, 1H, J=7.5 Hz), 7.70 (d, 2H, J=8.0 Hz), 7.53 (dd, 1H, J=7.5, 8.4 Hz), 7.23 (d, 2H, J=8.0 Hz), 7.11 (dd, 1H, J=1.7, 2.5 Hz), 6.86 (dd, 1H, J=1.7, 4.0 Hz), 6.31 (dd, 1H, J=2.5, 4.0 Hz), 5.91 (s, 2H), 2.41 (s, 3H).
Reference: [1] Patent: US2003/181496, 2003, A1,
  • 13
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Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 8, p. 2084 - 2093
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1996, p. 1699 - 1704
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 6, p. 1565 - 1569
[4] Bulletin de la Societe Chimique de France, 1917, vol. <4> 21, p. 111
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Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 29, p. 9109 - 9116
  • 15
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  • [ 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
  • 16
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  • [ 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
  • 17
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YieldReaction ConditionsOperation in experiment
10% at 60℃; for 3 h; Treatment of 1 (459 mg, 3.03 mmol) and NBS (677 mg, 3.80 mmol) in H2SO4 (3.0 mL) at 60 oC as described above afforded the following fractions in order of elution: (I) 7 (21 mg, 0.07 mmol, 2percent); (II) 2 (66 mg, 9percent) and 4 (24 mg, 3percent); (III): 2 (5 mg, 0.7percent) and 3,4-dibromo-2-nitrobenzaldehyde 6 (85 mg, 9percent); (IV) 5 (59 mg, 8percent), 8 (13 mg, 1percent), and 1 (18 mg, 4percent); (V) 3 (20 mg, 0.09 mmol, 3percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 18
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  • [ 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
  • 19
  • [ 109513-33-9 ]
  • [ 20357-21-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1996, p. 1699 - 1704
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 6, p. 1565 - 1569
  • 20
  • [ 109513-33-9 ]
  • [ 20357-21-5 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 8, p. 2084 - 2093
  • 21
  • [ 109019-72-9 ]
  • [ 20357-21-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1996, p. 1699 - 1704
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 6, p. 1565 - 1569
  • 22
  • [ 109513-33-9 ]
  • [ 20357-21-5 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 3807
  • 23
  • [ 20357-21-5 ]
  • [ 135484-74-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 6, p. 1565 - 1569
[2] Journal of the American Chemical Society, 2003, vol. 125, # 8, p. 2084 - 2093
  • 24
  • [ 20357-21-5 ]
  • [ 181871-83-0 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 8, p. 2084 - 2093
  • 25
  • [ 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
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3-Bromo-5-nitrobenzaldehyde

Similarity: 0.92

Chemical Structure| 5274-71-5

[ 5274-71-5 ]

2-Bromo-4-nitrobenzaldehyde

Similarity: 0.90

Chemical Structure| 90407-21-9

[ 90407-21-9 ]

2-Bromo-3-nitrobenzaldehyde

Similarity: 0.89

Chemical Structure| 84459-32-5

[ 84459-32-5 ]

2-Bromo-5-nitrobenzenecarbaldehyde

Similarity: 0.89

Bromides

Chemical Structure| 5551-12-2

[ 5551-12-2 ]

4-Bromo-2-nitrobenzaldehyde

Similarity: 0.97

Chemical Structure| 355134-13-3

[ 355134-13-3 ]

3-Bromo-5-nitrobenzaldehyde

Similarity: 0.92

Chemical Structure| 5274-71-5

[ 5274-71-5 ]

2-Bromo-4-nitrobenzaldehyde

Similarity: 0.90

Chemical Structure| 90407-21-9

[ 90407-21-9 ]

2-Bromo-3-nitrobenzaldehyde

Similarity: 0.89

Chemical Structure| 84459-32-5

[ 84459-32-5 ]

2-Bromo-5-nitrobenzenecarbaldehyde

Similarity: 0.89

Aldehydes

Chemical Structure| 5551-12-2

[ 5551-12-2 ]

4-Bromo-2-nitrobenzaldehyde

Similarity: 0.97

Chemical Structure| 355134-13-3

[ 355134-13-3 ]

3-Bromo-5-nitrobenzaldehyde

Similarity: 0.92

Chemical Structure| 5274-71-5

[ 5274-71-5 ]

2-Bromo-4-nitrobenzaldehyde

Similarity: 0.90

Chemical Structure| 90407-21-9

[ 90407-21-9 ]

2-Bromo-3-nitrobenzaldehyde

Similarity: 0.89

Chemical Structure| 84459-32-5

[ 84459-32-5 ]

2-Bromo-5-nitrobenzenecarbaldehyde

Similarity: 0.89

Nitroes

Chemical Structure| 5551-12-2

[ 5551-12-2 ]

4-Bromo-2-nitrobenzaldehyde

Similarity: 0.97

Chemical Structure| 355134-13-3

[ 355134-13-3 ]

3-Bromo-5-nitrobenzaldehyde

Similarity: 0.92

Chemical Structure| 5274-71-5

[ 5274-71-5 ]

2-Bromo-4-nitrobenzaldehyde

Similarity: 0.90

Chemical Structure| 90407-21-9

[ 90407-21-9 ]

2-Bromo-3-nitrobenzaldehyde

Similarity: 0.89

Chemical Structure| 84459-32-5

[ 84459-32-5 ]

2-Bromo-5-nitrobenzenecarbaldehyde

Similarity: 0.89