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[ CAS No. 128851-73-0 ]

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2D
Chemical Structure| 128851-73-0
Chemical Structure| 128851-73-0
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Product Details of [ 128851-73-0 ]

CAS No. :128851-73-0MDL No. :MFCD08669477
Formula : C8H5BrO Boiling 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:WarningClass:N/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   1~9

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YieldReaction ConditionsOperation in experiment
91.2%
Stage #1: With n-butyllithium In tetrahydrofuran at -65 - -60℃; for 4 h;
Stage #2: at -65℃; for 5 h;
5.28 g (0.0268 mol) of 6-bromobenzofuran was added to a 250 mL three-necked flask, 80 ml of dry tetrahydrofuran was added, stirred and dissolved, then placed in a freezer to cool to -65 ° C, n-butyllithium was added dropwise (2M) 14.74mL, maintained the temperature at -60 °C during the addition process, and dropwise addition completion in 1h. After the reaction was continued for 3 hours, 2.89 g (0.0321 mol) of dimethyl carbonate was added dropwise under this reaction conditions, and the dropwise addition was completed in 1 hour, and the reaction temperature was controlled to -65 ° C. After the reaction for 4 hours, the reaction was completed. and the reaction was quenched by dropwise addition of a saturated ammonium chloride solution under a low temperature condition. The reaction was quenched by dropwise addition of a saturated ammonium chloride solution under a low temperature condition, after the solvent was evaporated under reduced pressure, residue was stirred by adding 100ml of water and 100 ml of dichloromethane , and then the layers were separated. The organic layer was washed twice with saturated brine, 100 mL each time, and the dichloromethane layer was dried over anhydrous magnesium sulfate and filtered, dichloromethane was evaporated under reduced pressure to obtain 6-methyl formate benzofuran 4.3g. yield 91.2percent and HPLC purity 97.2percent.
Reference: [1] Patent: CN108129430, 2018, A, . Location in patent: Paragraph 0008; 0016; 0018; 0020
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YieldReaction ConditionsOperation in experiment
46% With polyphosphoric acid (PPA) In toluene at 20℃; for 4 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 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 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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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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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
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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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Reference: [1] Patent: WO2015/66371, 2015, A1,
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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] Patent: WO2015/66371, 2015, A1,
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