[ CAS No. 133720-60-2 ]

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2D
Chemical Structure| 133720-60-2
Chemical Structure| 133720-60-2
Structure of 133720-60-2

Quality Control of [ 133720-60-2 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 133720-60-2 ]

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Product Details of [ 133720-60-2 ]

CAS No. :133720-60-2MDL No. :MFCD09056756
Formula :C8H5BrOBoiling Point :233.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :GPZPQJITKRSVQJ-UHFFFAOYSA-N
M.W :197.03Pubchem ID :113628
Synonyms :

Computed Properties of [ 133720-60-2 ]

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

Safety of [ 133720-60-2 ]

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

Application In Synthesis of [ 133720-60-2 ]

  • Upstream synthesis route of [ 133720-60-2 ]
  • Downstream synthetic route of [ 133720-60-2 ]

[ 133720-60-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 253429-15-1 ]
  • [ 133720-60-2 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With PPA In chlorobenzene for 2.15 h; Heating / reflux
Stage #2: With sodium hydroxide In water; chlorobenzene at 20℃;
Scheme I,
step B:
Polyphosphoric acid (60 g) and chlorobenzene (100 mL) were combined and heated to reflux. To the refluxing mixture was added dropwise 2-(2-bromophenol) acetaldehyde diethyl acetal (27 g, 0.093 mol, prepared above in Scheme I, step A) dissolved in chlorobenzene (20 mL), over 15 minutes. Heating of the reaction mixture at reflux was continued for 2 hours and then it was cooled to room temperature. 1N sodium hydroxide (100 mL), was added and the reaction was stirred at room temperature overnight. The reaction mixture was then extracted with diethyl ether (3.x.100 mL), the organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (hexane, silica gel) to provide the 7-bromobenzo(b)furan (13.4 g, 73percent) as a clear oil.
58% With polyphosphoric acid In 1,2-dichloro-ethane at 83℃; for 3.00 h; Inert atmosphere 1-Bromo-2-(2,2-diethoxyethoxy)benzene (0102-3)(3.33g, 11.56mol, 1.0 equivalent)Soluble in DCE (60ml), add PPA(11.72g, 34.68mmol, 3.0 equivalents),The air in the round bottom flask was replaced with nitrogen three times and then refluxed at 83 ° C for 3 hours.After the reaction was completed, dichloromethane (100 ml) was added, and water (100 ml × 3) was washed.The organic phase was dried over anhydrous sodium sulfate and concentrated.Then purified by silica gel column chromatography (petroleum ether = 100percent) to give pale-yellow solid product 7-bromobenzofuran(1.336 g, yield: 58percent).
38%
Stage #1: With PPA In chlorobenzene for 1.67 h; Heating / reflux
Stage #2: With sodium hydroxide In water; chlorobenzene at 20℃;
A stirred mixture of polyphosphoric acid (~5 g) and chlorobenzene (8 mL) was heated at reflux and a solution of l-(2,2-diethoxyelhoxy)-2-bromobenzene (2.62 g, 9.0 mmol) in chlorobenzene (3 mL) was added dropwise over 10 min. The mixture was heated at reflux for 1.5 h. The mixture was allowed to cool to rt and IM aq NaOH (20 mL) was added, followed by ether (175 mL). The mixture was washed with water (2 x 20 mL) and brine (20 mL), and dried over MgSO4. Evaporation of the solvent left a residue which was purified by a chromatography on a 140-g silica cartridge eluted with hexanes and a 0-10percent EtOAc in hexanes gradient. Appropriate fractions were pooled and concentrated to afford 7-bromobenzofuran (0.65 g, 38percent from 2-bromophenol) as a clear colorless oil.
Reference: [1] Patent: US6353008, 2002, B1. Location in patent: Page column 38
[2] Patent: CN108658908, 2018, A. Location in patent: Paragraph 0160; 0162
[3] Patent: WO2007/117560, 2007, A2. Location in patent: Page/Page column 140-141
[4] Heterocyclic Communications, 2010, vol. 16, # 4-6, p. 249 - 252
[5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 7, p. 2007 - 2017
[6] Patent: WO2015/95261, 2015, A1. Location in patent: Page/Page column 36; 37
[7] Patent: WO2015/89842, 2015, A1. Location in patent: Page/Page column 36-37
[8] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6564 - 6567
  • 2
  • [ 253429-15-1 ]
  • [ 133720-60-2 ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydroxide; PPA In chlorobenzene Preparation of 7-Bromobenzo(b)furan
Scheme 1, step B: Polyphosphoric acid (60 g) and chlorobenzene (100 mL) were combined and heated to reflux.
To the refluxing mixture was added dropwise 2-(2-bromophenol) acetaldehyde diethyl acetal (27 g, 0.093 mol, prepared above in Scheme I, step A) dissolved in chlorobenzene (20 mL) over 15 minutes.
Heating of the reaction mixture at reflux was continued for 2 hours and then it was cooled to room temperature. 1N sodium hydroxide (100 mL) was added and the reaction was stirred at room temperature overnight.
The reaction mixture was then extracted with diethyl ether (3*100 mL), the organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum.
The residue was purified by flash chromatography (hexane, silica gel) to provide the 7-bromobenzo(b)furan (13.4 g, 73percent) as a clear oil.
Reference: [1] Patent: US6465453, 2002, B1
  • 3
  • [ 204452-94-8 ]
  • [ 128851-73-0 ]
  • [ 133720-60-2 ]
Reference: [1] Patent: US2010/280013, 2010, A1. Location in patent: Page/Page column 42
[2] Patent: WO2015/66371, 2015, A1. Location in patent: Paragraph 00384-00385
  • 4
  • [ 95-56-7 ]
  • [ 133720-60-2 ]
Reference: [1] Heterocyclic Communications, 2010, vol. 16, # 4-6, p. 249 - 252
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 7, p. 2007 - 2017
[3] Patent: WO2015/95261, 2015, A1
[4] Patent: WO2015/89842, 2015, A1
[5] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6564 - 6567
[6] Patent: CN103724305, 2016, B
[7] Patent: WO2007/117560, 2007, A2
[8] Patent: CN108658908, 2018, A
  • 5
  • [ 95-56-7 ]
  • [ 128868-60-0 ]
  • [ 133720-60-2 ]
Reference: [1] Patent: EP1204654, 2003, B1
[2] Patent: EP1204654, A1[2] Patent: , 2002,
  • 6
  • [ 591-20-8 ]
  • [ 128851-73-0 ]
  • [ 133720-60-2 ]
Reference: [1] Patent: WO2015/66371, 2015, A1
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