[ CAS No. 23145-07-5 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 23145-07-5
Chemical Structure| 23145-07-5
Structure of 23145-07-5

Quality Control of [ 23145-07-5 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 23145-07-5 ]

SDS

Product Details of [ 23145-07-5 ]

CAS No. :23145-07-5MDL No. :MFCD03407317
Formula :C8H5BrOBoiling Point :233.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :AYOVPQORFBWFNO-UHFFFAOYSA-N
M.W :197.03Pubchem ID :90015
Synonyms :

Computed Properties of [ 23145-07-5 ]

TPSA : 13.1 H-Bond Acceptor Count : 1
XLogP3 : 3 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 23145-07-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 23145-07-5 ]

  • Upstream synthesis route of [ 23145-07-5 ]

[ 23145-07-5 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 112598-18-2 ]
  • [ 23145-07-5 ]
YieldReaction ConditionsOperation in experiment
85% With PPA In benzene for 4.00 h; Heating / reflux To a solution of the product from Step A (8.4g) in benzene (50ML) was added POLYPHOSPHORIC acid (10G). The mixture was heated at reflux for 4 hrs. The reaction was cooled to 0°C and poured into ice water (80ML) and extracted with ether. The ether layer was washed with saturated sodium bicarbonate and brine, dried with MGS04, filtered and concentrated in vacuo to give 4.9g of crude product (85percent).
85% With PPA In benzene for 4.00 h; Heating / reflux To a solution ol the product from Step A (8.4 g) in benzene (50 ml) was added polyphosphoric acid (10 g). The mixture was heated at reflux lor 4 hrs. The reaction was cooled to 0 C. and poured into ice water (80 ml) and extracted with ether. The ether layer was washed with saturated sodium bicarbonate and brine, dried with MgSO4, filtered and concentrated in vacuo to give 4.9 g ol crude product (85percent)
85%
Stage #1: With phosphoric acid In benzene at 0℃; for 4.00 h; Heating / reflux
To a solution of the product from Step A (8.4 g) in benzene (50 ml) was added polyphosphoric acid (10 g). The mixture was heated at reflux for 4 hrs. The reaction was cooled to 0 C. and poured into ice water (80 ml) and extracted with ether. The ether layer was washed with saturated sodium bicarbonate and brine, dried with MgSO4, filtered and concentrated in vacuo to give 4.9 g of crude product (85percent)
85% With PPA In benzene for 4.00 h; Heating / reflux Step B; To a solution of the product from Step A (8.4g) in benzene (50ml) was added polyphosphoric acid (10g). The mixture was heated at reflux for 4 hrs. The reaction was cooled to 0°C and poured into ice water (80ml) and extracted with ether. The ether layer was washed with saturated sodium bicarbonate and brine, dried with MgS04, filtered and concentrated in vacuo to give 4.9g of crude product (85percent)
85% With PPA In benzene for 4.00 h; Heating / reflux To a solution of the product from Step A (8.4g) in benzene (50mut) was added polyphosphoric acid (10g). The mixture was heated at reflux for 4 hrs. The reaction was cooled to 0°C and poured into ice water (80ml) and extracted with ether. The ether layer was washed with saturated sodium bicarbonate and brine, dried with MgS04, filtered and concentrated in vacuo to give 4.9g of crude product (85percent)
77% for 3.00 h; Reflux General procedure: A 25 mL round-bottomed flask was charged with 2-aryloxyacetaldehyde diethyl acetals (1 mmol), Sn-b (0.1 g), andtrifluorotoluene (10 mL). The mixture was stirred under refluxingcondition and monitored by GC. Upon completion, the mixture wascooled to room temperature, and the catalyst Sn-b was filtrate off.The filter cake was washed with trifluorotoluene (10 mL3). Thecombined filtratewas concentrated under vacuum. The residuewaspurified by flash column chromatography on SiO2 (petroleumether/ethyl acetate) to afford the desired 2,3-unsubstituted benzo[b]furans.
59% With polyphosphoric acid In toluene for 3.00 h; Reflux Step 2.
5-Bromobenzofuran
A solution of 1-bromo-4-(2,2-diethoxyethoxy)benzene (5 g, 17.29 mmol, 1.00 equiv), polyphosphoric acid (13 g, 132.65 mmol, 8.00 equiv) and toluene (50 mL) was heated to reflux for 3 hr in an oil bath.
The resulting mixture was concentrated under vacuum, diluted with 50 mL of ethyl acetate, and washed with 3*50 mL of water and 2*50 mL of saturated sodium bicarbonate.
The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum.
The residue was applied onto a silica gel column (ethyl acetate/petroleum ether (1:10)).
This resulted in 2 g (59percent) of 5-bromobenzofuran as a yellow oil.
1H-NMR (300 MHz, CDCl3, ppm): 7.759-7.751 (d, J=2.4 Hz, 1H), 7.649-7.642 (d, J=2.1 Hz, 1H), 7.442-7.381 (s, 2H), 6.748-6.741 (s, 1H)
50% With PPA In chlorobenzene for 16.00 h; Heating / reflux Phosphoric acid (40 g) was added to a solution of l-bromo-4-(2,2-diethoxyethoxy)benzene (51.9 mmol) in chlorobenzene (80 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was allowed to cool to rt and the chlorobenzene layer was decanted. The residue was washed with toluene (2 x 30 mL) and the combined organic layers were concentrated. The residue was purified by Flash chromatography (hexane) to provide 5-bromobenzofuran in 50percent yield as colorless oil.
50% With phosphoric acid In chlorobenzene for 16.00 h; Reflux 2. Synthesis of 5-bromobenzofuran.Phosphoric acid (40 g) was added to a solution of l-bromo-4-(2,2- diethoxyethoxy)benzene (51.9 mmol) in chlorobenzene (80 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was allowed to cool to rt and the chlorobenzene layer was decanted. The residue was washed with toluene (2 x 30 mL) and the combined organic layers were concentrated. The residue was purified by Flash chromatography (hexane) to provide 5-bromobenzofuran in 50percent yield as colorless oil.
50% With phosphoric acid In chlorobenzene for 16.00 h; Reflux 2. Synthesis of 5-bromobenzofuran.Phosphoric acid (40 g) was added to a solution of l-bromo-4-(2,2- diethoxyethoxy)benzene (51.9 mmol) in chlorobenzene (80 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was allowed to cool to rt and the chlorobenzene layer was decanted. The residue was washed with toluene (2 x 30 mL) and the combined organic layers were concentrated. The residue was purified by Flash chromatography (hexane) to provide 5-bromobenzofuran in 50percent yield as colorless oil.

Reference: [1] Patent: WO2004/33440, 2004, A1. Location in patent: Page 239-240
[2] Patent: US2004/147559, 2004, A1. Location in patent: Page 122
[3] Patent: US2004/106794, 2004, A1. Location in patent: Page 123
[4] Patent: WO2005/66147, 2005, A1. Location in patent: Page/Page column 209
[5] Patent: WO2005/68460, 2005, A1. Location in patent: Page/Page column 203
[6] Tetrahedron, 2015, vol. 71, # 29, p. 4835 - 4841
[7] Patent: US2012/277224, 2012, A1. Location in patent: Page/Page column 15-16
[8] Patent: WO2009/23844, 2009, A2. Location in patent: Page/Page column 133
[9] Patent: WO2010/21797, 2010, A1. Location in patent: Page/Page column 98
[10] Patent: WO2010/24980, 2010, A1. Location in patent: Page/Page column 116
[11] Journal of Medicinal Chemistry, 1997, vol. 40, # 3, p. 322 - 330
[12] Heterocyclic Communications, 2010, vol. 16, # 4-6, p. 249 - 252
[13] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6564 - 6567
[14] European Journal of Organic Chemistry, 2018, vol. 2018, # 22, p. 2774 - 2779
  • 2
  • [ 129969-69-3 ]
  • [ 23145-07-5 ]
YieldReaction ConditionsOperation in experiment
25%
Stage #1: With phosphoric acid In water at 100℃;
Stage #2: With sodium carbonate In water
A mixture of l-bromo-4-(2,2-dimethoxyethoxy)benzene (200 mmol) and polyphosphoric acid (30 mL) was heated to 100 °C and stirred overnight. The reaction mixture was cooled to room temperature and poured into aqueous sodium carbonate until the pH was ~7 to 8. Then the mixture was extracted with dichloromethane (4 x 100 mL) and the organic layers were combined, washed with water (100 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The mixture was distilled under reduced pressure (95 °C, 5 mm Hg) to give a clear oil as the title product (25percent). .H NMR (300 MHz, DMSO-i 6): δ 8.04 (s, 1 H), 7.87 (s, 1 H), 7.59 (d, J= 8.4 Hz, 1 H), 7.44 (d, J= 8.4 Hz, 1 H), 6.95 (s, 1 H).
179 g for 28.00 h; Reflux Chlorobenzene (1200 mL) was added to a 5000 mL three-necked bottomed flask and the crude crude 1-bromo-4 '- (2,2-dimethoxyethyl) benzene (350 g) (870 g).Stirring was started and heated to reflux for 28 hours.TLC and GC tracking reactions.After completion of the reaction, the reaction solution was cooled to room temperature and the lower layer was separated.The organic phase was washed with water (600 mL) and sodium hydroxide (2 mol / L, 600 mL).Dried over sodium sulfate overnight.Distillation to remove most of the chlorobenzene.The crude product 5-bromobenzofuran (245 g) was then distilled under reduced pressure.After the distillation of pure 5-bromobenzofuran 179 g, the yield of 74.9percent.
Reference: [1] Patent: WO2011/66211, 2011, A1. Location in patent: Page/Page column 52
[2] Journal of Materials Chemistry, 2001, vol. 11, # 11, p. 2759 - 2772
[3] Patent: CN103724304, 2016, B. Location in patent: Paragraph 0022; 0024
  • 3
  • [ 24589-89-7 ]
  • [ 108-24-7 ]
  • [ 23145-07-5 ]
YieldReaction ConditionsOperation in experiment
40% at 100℃; for 20.00 h; Heating / reflux To a mixture of 2-formyl-4-bromophenoxy acetic acid [(50G,] 0. [192MOL),] sodium acetate [(100G,] 1. 21mol) in acetic acid (250mL) at [100°C] was added acetic anhydride [(LOOML)] portions during a period of 3h. The reaction mixture was then refluxed for 20h. The solvent was removed by distillation and residue diluted with 3N HCl [(500ML)] and refluxed for 2h. The reaction mixture was then concentrated under vacuum and product extracted with pet. ether [(3X200ML).] The organic layer was washed with 10percent [NAHC03] solution and evaporated to give [5-BROMO-1-BENZOFURAN] [(15G,] 40percent) as a pale yellow liquid.
Reference: [1] Patent: WO2004/7491, 2004, A1. Location in patent: Page 51-52
  • 4
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  • [ 128868-60-0 ]
Reference: [1] Patent: US2018/170909, 2018, A1. Location in patent: Paragraph 0818; 0819
  • 5
  • [ 66826-78-6 ]
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Reference: [1] Heterocycles, 1997, vol. 45, # 9, p. 1657 - 1661
  • 6
  • [ 7252-83-7 ]
  • [ 106-41-2 ]
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Reference: [1] Patent: US5700809, 1997, A
  • 7
  • [ 863659-59-0 ]
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Reference: [1] Tetrahedron, 2005, vol. 61, # 32, p. 7746 - 7755
  • 8
  • [ 96853-37-1 ]
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Reference: [1] Synlett, 2006, # 4, p. 567 - 570
  • 9
  • [ 106-41-2 ]
  • [ 23145-07-5 ]
Reference: [1] Heterocyclic Communications, 2010, vol. 16, # 4-6, p. 249 - 252
[2] Patent: US2012/277224, 2012, A1
[3] Patent: WO2011/66211, 2011, A1
[4] Tetrahedron, 2015, vol. 71, # 29, p. 4835 - 4841
[5] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6564 - 6567
[6] Patent: CN103724304, 2016, B
[7] European Journal of Organic Chemistry, 2018, vol. 2018, # 22, p. 2774 - 2779
  • 10
  • [ 271-89-6 ]
  • [ 23145-07-5 ]
  • [ 23145-08-6 ]
Reference: [1] Heterocycles, 2001, vol. 54, # 2, p. 825 - 831
  • 11
  • [ 106-41-2 ]
  • [ 23145-07-5 ]
  • [ 128868-60-0 ]
Reference: [1] Patent: EP1204654, 2003, B1
[2] Patent: EP1204654, A1[2] Patent: , 2002,
  • 12
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Reference: [1] Synlett, 2006, # 4, p. 567 - 570
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  • [ 1761-61-1 ]
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Reference: [1] Synlett, 2006, # 4, p. 567 - 570
  • 14
  • [ 104743-20-6 ]
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Reference: [1] Tetrahedron, 2005, vol. 61, # 32, p. 7746 - 7755
  • 15
  • [ 13997-74-5 ]
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Reference: [1] Tetrahedron, 2005, vol. 61, # 32, p. 7746 - 7755
  • 16
  • [ 79-11-8 ]
  • [ 1761-61-1 ]
  • [ 23145-07-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1900, vol. 312, p. 332
  • 17
  • [ 591-20-8 ]
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Reference: [1] Patent: US2018/170909, 2018, A1
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