[ CAS No. 128851-73-0 ]

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2D
Chemical Structure| 128851-73-0
Chemical Structure| 128851-73-0
Structure of 128851-73-0

Quality Control of [ 128851-73-0 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 128851-73-0 ]

SDS

Product Details of [ 128851-73-0 ]

CAS No. :128851-73-0MDL No. :MFCD08669477
Formula :C8H5BrOBoiling Point :233.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :197.03Pubchem ID :15158722
Synonyms :

Computed Properties of [ 128851-73-0 ]

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

Safety of [ 128851-73-0 ]

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 [ 128851-73-0 ]

  • Upstream synthesis route of [ 128851-73-0 ]
  • Downstream synthetic route of [ 128851-73-0 ]

[ 128851-73-0 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
46% With polyphosphoric acid (PPA) In toluene at 20℃; for 4.00 h; Inert atmosphere; Reflux Polyphosphoric acid (PPA) (0.743 g, 6.83 mmol) was added to asolution of 175 (0.656 g, 2.28 mmol) in toluene (4.6 mL) at roomtemperature under Ar. The mixture was headed until reflux began,this being maintained for 4 h, then cooled to room temperature,quenched with cooled H2O and extracted with EtOAc. The organiclayers were washed with brine, dried (MgSO4), filtered and concentratedin vacuo. The crude product was purified by silica gel CC(EtOAc/hexane, 2:98) to give 6-bromobenzofuran (176) (major,0.206 g, 1.05 mmol, 46percent) and 4-bromobenzofuran (177) (minor,0.183 g, 0.935 mmol, 41percent) as colorless oils: 176: 1H-NMR (CDCl3,400 MHz) d: 1H-NMR (CDCl3, 400 MHz) d: 6.75 (d, J = 1.6 Hz, 1H,furan-H), 7.36 (dd, J = 1.2, 8.4 Hz, 1H, Ar–H), 7.46 (d, J = 8.4 Hz,1H, Ar–H), 7.60 (d, J = 1.6 Hz, 1H, furan-H), 7.69 (s, 1H, Ar–H);177: 1H-NMR (CDCl3, 400 MHz) d: 6.82 (d, J = 2.4 Hz, 1H, furan-H), 7.17 (dd, J = 7.6, 8.4 Hz, Ar–H), 7.40 (d, J = 7.6 Hz, 1H, Ar–H),7.45 (d, J = 8.4 Hz, 1H, Ar–H), 7.66 (d, J = 2.4 Hz, 1H, furan-H).
15% With polyphosphoric acid In chlorobenzene at 80℃; for 2.00 h; A mixture of 17 gm (57.8 mMol) 2-(3-bromophenoxy)acetaldehyde diethyl acetal and 17.5 gm polyphosphoric acid in 400 mL chlorobenzene was heated to 80° C. for 2 hours. The reaction mixture was cooled to room temperature and the chlorobenzene was decanted from the polyphosphoric acid. The polyphosphoric acid was washed with two 150 mL portions of diethyl ether. All or the organic phases were combined and concentrated under reduced pressure. The residue was redissolved in diethyl ether and the organic phases were washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residual oil was subjected to silica gel chromatography, eluting with hexane.Fractions containing the faster eluting isomer were combined and concentrated under reduced pressure to provide 1.7 gm (15percent) 4-bromobenzofuran.EA: Calculated for C8H5BrO: Theory: C, 48.77; H, 2.56. Found: C, 48.89; H, 2.72.Fractions containing the slower eluting isomer were combined and concentrated under reduced pressure to provide 2.5 gm (22percent) 6-bromobenzofuran.EA: Calculated for C8H5BrO: Theory: C, 48.77; H, 2.56. Found: C, 48.89; H, 2.67.
15% With PPA In chlorobenzene at 80℃; for 2.00 h; A mixture of 17 gm (57.8 mMol) 2-(3-bromophenoxy)acetaldehyde diethyl acetal and 17.5 gm polyphosphoric acid in 400 mL chlorobenzene was heated to 80°C for 2 hours. The reaction mixture was cooled to room temperature and the chlorobenzene was decanted from the polyphosphoric acid. The polyphosphoric acid was washed with two 150 mL portions of diethyl ether. All or the organic phases were combined and concentrated under reduced pressure. The residue was redissolved in diethyl ether and the organic phases were washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residual oil was subjected to silica gel chromatography, eluting with hexane. Fractions containing the faster eluting isomer were combined and concentrated under reduced pressure to provide 1.7 gm (15percent) 4-bromobenzofuran. EA: Calculated for C8H5BrO: Theory: C, 48.77; H, 2.56. Found: C, 48.89; H, 2.72. Fractions containing the slower eluting isomer were combined and concentrated under reduced pressure to provide 2.5 gm (22percent) 6-bromobenzofuran. EA: Calculated for C8H5BrO: Theory: C, 48.77; H, 2.56. Found: C, 48.89; H, 2.67.
Reference: [1] Phytochemistry, 2013, vol. 96, p. 132 - 147
[2] Patent: US7045545, 2006, B1. Location in patent: Page/Page column 20
[3] Patent: EP1204659, 2003, B1. Location in patent: Page/Page column 15-16
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 3, p. 322 - 330
[5] Tetrahedron, 2015, vol. 71, # 29, p. 4835 - 4841
[6] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3215 - 3230
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  • [ 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
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Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 3, p. 322 - 330
[2] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6564 - 6567
[3] Patent: EP1204659, 2003, B1
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  • [ 591-20-8 ]
  • [ 128851-73-0 ]
  • [ 128868-60-0 ]
Reference: [1] Phytochemistry, 2013, vol. 96, p. 132 - 147
[2] Tetrahedron, 2015, vol. 71, # 29, p. 4835 - 4841
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3215 - 3230
  • 5
  • [ 204452-94-8 ]
  • [ 128851-73-0 ]
Reference: [1] Heterocyclic Communications, 2010, vol. 16, # 4-6, p. 249 - 252
[2] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6564 - 6567
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  • [ 133720-60-2 ]
Reference: [1] Patent: WO2015/66371, 2015, A1
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