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[ CAS No. 1761-61-1 ]

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Chemical Structure| 1761-61-1
Chemical Structure| 1761-61-1
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CAS No. :1761-61-1MDL No. :MFCD00003330
Formula : C7H5BrO2 Boiling Point : 247.3°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :201.02Pubchem ID :72863
Synonyms :

Computed Properties of [ 1761-61-1 ]

TPSA : 37.3 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 1761-61-1 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1761-61-1 ]

  • Upstream synthesis route of [ 1761-61-1 ]
  • Downstream synthetic route of [ 1761-61-1 ]

[ 1761-61-1 ] Synthesis Path-Upstream   1~10

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Reference: [1] Synlett, 2006, # 4, p. 567 - 570
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  • [ 23145-07-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1900, vol. 312, p. 332
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  • [ 17345-77-6 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 128, p. 105583 - 105586
[2] Journal of Materials Chemistry, 2007, vol. 17, # 14, p. 1399 - 1411
[3] Chemistry - A European Journal, 2009, vol. 15, # 37, p. 9530 - 9542
[4] Journal of Materials Chemistry C, 2018, vol. 6, # 16, p. 4471 - 4478
[5] Green Chemistry, 2015, vol. 17, # 9, p. 4533 - 4536
[6] European Journal of Organic Chemistry, 2016, vol. 2016, # 16, p. 2802 - 2814
[7] European Journal of Organic Chemistry, 2014, vol. 2014, # 5, p. 1037 - 1046
[8] European Journal of Organic Chemistry, 2014, vol. 2014, # 5, p. 1037 - 1046
[9] Tetrahedron Letters, 2005, vol. 46, # 19, p. 3357 - 3358
[10] Journal of Organic Chemistry, 2011, vol. 76, # 4, p. 1013 - 1030
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Reference: [1] American Chemical Journal, 1909, vol. 42, p. 495
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  • [ 16740-73-1 ]
Reference: [1] Drug Metabolism and Disposition, 2012, vol. 40, # 10, p. 2002 - 2008,7
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  • [ 16634-88-1 ]
YieldReaction ConditionsOperation in experiment
82% at 32℃; for 1 h; [000244] To a solution of Compound Dl (80 g, 266 mmol) in CH3C02H (400 ml) was added fuming HN03 (24 mL) at 10 °C and the mixture was stirred at 32 °C for 1 h. Water (200 mL) was added and the mixture filtered. The filtrate was washed with water to remove CH3CO2H and was dried to give Compound D2 (80 g, yield 82percent) as a yellow solid. LC-MS (m/z): 244 [M-l]~.
60% With nitric acid In water; acetic acid at 60 - 65℃; for 1.16667 h; The first step was the nitration of 5-bromo-2-hydroxybenzaldehyde (1*) yielding 5- bromo-2-hydroxy-3-nitrobenzaldehyde (2*) : 0 0 Br HN03 Br H H OH ACOH OH step 1 (1*) recryst. (2*) (step 1a) A solution of 1.0 mol of 5-bromo-2-hydroxybenzaldehyde (1*) in 3.75 litres acetic acid (98percent) was formed on heating the mixture to about 60°C. 1.5 mol of concentrated nitric acid (137 g = 97 ml) was added slowly in approximately 1 hour. After the completion of the addition stirring was continued at 65 °C for a further 10 minutes. The solution was then cooled to 45 °C, and the product was precipitated by the addition of 4 litres of water. After stirring for at least 3 hours the product was collected on a filter and washed with water until the pH of the mother liquor was approximately 6. The material is dried as much as possible by centrifugation. The crude product was dissolved in 800 ml acetone under refluxing and stirring. 400 mi acetone was removed by distillation. After cooling to 20°C, the mixture was stirred for 3 hours. The precipitate was collected on a filter an d washed with petroleum ether 40-65°C. The solid was dried overnight in an air stream at 40°C. Finally, the crude (2*) was recrystallized from acetone to yield an end product with a purity of 98percent as shown by NMR analysis. 5-bromo-2-hydroxybenzaidehyde (1*) was identified by its characteristic chemical shift 8 9.84 ppm; 5-bromo-2-hydroxy-3-nitrobenzaldehyde (2*) had a characteristic chemical shift of 8 10. 4 ppm. The overall yield of this step was approximately 60percent (crude on crude).
60% With nitric acid In water; acetic acid at 60 - 65℃; for 1.16667 h; The first step was the nitration of 5-bromo-2-hydroxybenzaldehyde (1*) yielding 5- bromo-2-hydroxy-3-nitrobenzaldehyde (2*) : 0 Br HN03 Br I H I w OH Ar OH OH step 1 "Nn sfep'"-'2 (1*) recryst. (2*) (step la) A solution of 1.0 mol of 5-bromo-2-hydroxybenzaldehyde (1*) in 3.75 litres acetic acid (98percent) was formed on heating the mixture to about 60°C. 1. 5 mol of concentrated nitric acid (137 g = 97 mi) was added slowly in approximately 1 hour. After the completion of the addition stirring was continued at 65 °C for a further 10 minutes. The solution was then cooled to 45 °C, and the product was precipitated by the addition of 4 litres of water. After stirring for at least 3 hours the product was collected on a filter and washed with water until the pH of the mother liquor was approximately 6. The material is dried as much as possible by centrifugation. The crude product was dissolved in 800 mi acetone under refluxing and stirring. 400 mi acetone was removed by distillation. After cooling to 20°C, the mixture was stirred for 3 hours. The precipitate was collected on a filter and washed with petroleum ether 40-65°C. The solid was dried overnight in an air stream at 40°C. Finally, the crude (2*) was recrystallized from acetone to yield an end product with a purity of 98percent as shown by NMR analysis. 5-bromo-2-hydroxybenzaldehyde (1*) was identified by its characteristic chemical shift 8 9.84 ppm; 5-bromo-2-hydroxy-3-nitrobenzaldehyde (2*) had a characteristic chemical shift of 8 10.4 ppm. The overall yield of this step was approximately 60percent (crude on crude).
60% With nitric acid In acetic acid at 60 - 65℃; for 1.16667 h; The first step was the nitration of 5-bromo-2-hydroxybenzaldehyde (1*) yielding 5- bromo-2-hydroxy-3-nitrobenzaldehyde (2*) : 0 0 Br HN03 Br H H OH AH OH step t No2 (1*) recryst. (2) (step 1a) A solution of 1.0 mol of 5-bromo-2-hydroxybenzaldehyde (1*) in 3. 75 litres acetic acid (98percent) was formed on heating the mixture to about 60C. 1.5 mol of concentrated nitric acid (137 g = 97 mi) was added slowly in approximately 1 hour. After the completion of the addition stirring was continued at 65C for a further 10 minutes. The solution was then cooled to 45C, and the product was precipitated by the addition of 4 litres of water. After stirring for at least 3 hours the product was collected on a filter and washed with water until the pH of the mother liquor was approximately 6. The material was dried as much as possible by centrifugation. The crude product was dissolved in 800 mi acetone under refluxing and stirring-400 m) acetone was removed by distillation. After cooling to 20C, the mixture was stirred for 3 hours. The precipitate was collected on a filter and washed with petroleum ether 40-65C. The solid was dried overnight In an air stream at 40C. Finally, the crude (2*) was recrystallized from acetone to yield an end product with a purity of 98percent as shown by NMR analysis. 5-bromo-2-hydroxybenzaldehyde (1*) was identified by its characteristic chemical shift 8 9.84 ppm; 5-bromo-2-hydroxy-3-nitrobenzaldehyde (2*) had a characteristic chemical shift of 8 10. 4 ppm. The overall yield of this step was approximately 60percent (crude on crude).
60% at 60 - 65℃; for 1.16667 h; A solution of 1.0 mol of 5-bromo-2-hydroxybenzaldehyde (1*) in 3.75 litres acetic acid (98percent) was formed on heating the mixture to about 60° C. 1.5 mol of concentrated nitric acid (137 g=97 ml) was added slowly in approximately 1 hour. After the completion of the addition stirring was continued at 65° C. for a further 10 minutes. The solution was then cooled to 45° C., and the product was precipitated by the addition of 4 litres of water. After stirring for at least 3 hours the product was collected on a filter and washed with water until the pH of the mother liquor was approximately 6. The material is dried as much as possible by centrifugation. The crude product was dissolved in 800 ml acetone under refluxing and stirring. 400 ml acetone was removed by distillation. After cooling to 20° C., the mixture was stirred for 3 hours. The precipitate was collected on a filter and washed with petroleum ether 40-65° C. The solid was dried overnight in an air stream at 40° C. Finally, the crude (2*) was recrystallized from acetone to yield an end product with a purity of 98percent as shown by NMR analysis. 5-bromo-2-hydroxybenzaldehyde (1*) was identified by its characteristic chemical shift δ 9.84 ppm; 5-bromo-2-hydroxy-3-nitrobenzaldehyde (2*) had a characteristic chemical shift of δ 10.4 ppm. The overall yield of this step was approximately 60percent (crude on crude)
42% at 85℃; for 2 h; 0.1 mol of 5-bromosalicylaldehyde was dissolved in 20 ml of acetic acid and the solution was heated to 85° C. with stirring. Under this condition, 6.9 ml of a 65percent nitric acid solution was added dropwise to the solution, which was added dropwise. Reaction 2h. After completion of the reaction, 50 ml of ice water was added to the solution to precipitate a yellow precipitate which was filtered and dried. After recrystallization from ethanol, a yellow needle-like solid was obtained with a yield of 42percent.

Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 35, p. 6460 - 6469
[2] Tetrahedron, 2003, vol. 59, # 46, p. 9239 - 9247
[3] Patent: WO2015/42397, 2015, A1, . Location in patent: Paragraph 000244
[4] Patent: WO2005/92340, 2005, A1, . Location in patent: Page/Page column 17-18
[5] Patent: WO2005/92339, 2005, A1, . Location in patent: Page/Page column 16-17
[6] Patent: WO2005/92338, 2005, A1, . Location in patent: Page/Page column 12-13
[7] Patent: US2006/13874, 2006, A1, . Location in patent: Page/Page column 2
[8] Patent: CN108069929, 2018, A, . Location in patent: Paragraph 0060-0061
[9] Chemische Berichte, 1904, vol. 37, p. 3934
[10] J. Prakt. Chem./Chem.-Ztg., 1998, vol. 340, # 6, p. 562 - 566
[11] Journal of Coordination Chemistry, 2015, vol. 68, # 13, p. 2296 - 2306
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Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 2, p. 340 - 342
[2] Tetrahedron, 2010, vol. 66, # 34, p. 6906 - 6911
[3] Applied Organometallic Chemistry, 2016, vol. 30, # 3, p. 116 - 124
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Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5823 - 5828
[2] Applied Organometallic Chemistry, 2016, vol. 30, # 3, p. 116 - 124
[3] New Journal of Chemistry, 2017, vol. 41, # 22, p. 13625 - 13646
  • 9
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YieldReaction ConditionsOperation in experiment
99% With potassium carbonate; caesium carbonate In <i>N</i>-methyl-acetamide Step A:
Synthesis of 5-bromo-2-isopropoxybenzaldehyde AX. To a suspension of potassium carbonate (34.4 g, 249 mmol) and cesium carbonate (16.2 g, 50 mmol) in dimethylformamide were added 5-bromosalicaldehyde (25.0 g, 124 mmol) and 2-iodopropane (25.0 mL, 249 mmol).
The suspension was stirred at room temperature overnight, then at 70° C. for 4 hrs.
The volatiles were removed, and the residue was partitioned between methyl t-butylether and water.
The aqueous layer was extracted with methyl t-butylether and the combined organic phases were washed with water, sodium hydroxide, and brine, and then dried over magnesium sulfate.
Concentration to dryness afforded compound AX (30.0 g) as a pale yellow oil in 99percent yield.
1H NMR (CDCl3, 400 MHz): δ 1.40 (d, J=6.3 Hz, 6H), 4.65 (sept., J=6.0 Hz, 1H), 6.89 (d, J=9.0 Hz, 1H), 7.59 (dd, J=9.0 and 2.7 Hz, 1H), 7.91 (d, J=2.7 Hz, 1H), 10.39 (s, 1H).
99% With potassium carbonate; caesium carbonate In N,N-dimethyl-formamide at 20 - 70℃; for 4 h; To a suspension of potassium carbonate (34.4 g, 249 mmol) and cesium carbonate (16.2 g, 50 mmol) in dimethylformamide were added 5-bromosalicaldehyde (25.0 g, 124 mmol) and 2-iodopropane (25.0 mL, 249 mmol).
The suspension was stirred at room temperature overnight, then at 70° C. for 4 hrs.
The volatiles were removed, and the residue was partitioned between methyl t-butylether and water.
The aqueous layer was extracted with methyl t-butylether and the combined organic phases were washed with water, sodium hydroxide, and brine, and then dried over magnesium sulfate.
Concentration to dryness afforded compound AX (30.0 g) as a pale yellow oil in 99percent yield. 1H NMR (CDCl3, 400 MHz): δ (ppm) 1.40 (d, J=6.3 Hz, 6H), 4.65 (sept., J=6.0 Hz, 1H), 6.89 (d, J=9.0 Hz, 1H), 7.59 (dd, J=9.0 and 2.7 Hz, 1H), 7.91 (d, J=2.7 Hz, 1H), 10.39 (s, 1H).
98% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 0.5 h; Inert atmosphere To a solution of 5-bromo-2-hydroxybenzaldehyde 3 (600 mg, 3.0mmol) and 2-iodopropane (1.4 ml, 15 mmol) in dry-DMF wasadded K2CO3 (3.2 g, 24 mmol). The mixture was heated at 60 Cunder N2 in oil bath. The mixture was stirred for 30 min. The excessK2CO3 was quenched with 1 M aq. HCl. After the addition 1 M aq.HCl, extracted with ethyl acetate and washed with brine. Theorganic layer was dried over Na2SO4, filtered and concentrated. The residue waspurified by column chromatography on silica gel (hexane / AcOEt = 20 : 1 ) to give5-bromo-2-isopropoxybenzaldehyde (712.6 mg, 98percent) as a colorless oil. 1H NMR (270MHz, CDCl3) δ 1.40 (d. J = 5.94 Hz, 6H), 4.58-4.71 (m, 1H), 6.89 (d, J = 9.2 Hz, 1H),7.59 (d, J = 8.6 Hz, 1H), 7.91 (s, 1H), 10.40 (s, 1H).
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[2] Tetrahedron Letters, 2010, vol. 51, # 4, p. 709 - 713
[3] Patent: US9115095, 2015, B2, . Location in patent: Page/Page column 44; 45
[4] Synlett, 2016, vol. 27, # 16, p. 2352 - 2356
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[9] Patent: US5750549, 1998, A,
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[11] Patent: US2011/9621, 2011, A1, . Location in patent: Page/Page column 6-7
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  • [ 75-26-3 ]
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  • [ 138505-25-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, p. 2783 - 2787
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 33, p. 4614 - 4627
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