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[ CAS No. 54450-20-3 ]

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2D
Chemical Structure| 54450-20-3
Chemical Structure| 54450-20-3
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Product Details of [ 54450-20-3 ]

CAS No. :54450-20-3MDL No. :MFCD06738724
Formula : C8H5BrO2 Boiling Point : 319.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :213.03Pubchem ID :10512748
Synonyms :

Computed Properties of [ 54450-20-3 ]

TPSA : 26.3 H-Bond Acceptor Count : 2
XLogP3 : 2.2 H-Bond Donor Count : 0
SP3 : 0.13 Rotatable Bond Count : 0

Safety of [ 54450-20-3 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 54450-20-3 ]

  • Upstream synthesis route of [ 54450-20-3 ]
  • Downstream synthetic route of [ 54450-20-3 ]

[ 54450-20-3 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 872191-26-9 ]
  • [ 54450-20-3 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: at 150℃; for 6 h;
Stage #2: With hydrogenchloride In methanol; water at 100℃; for 2 h;
To a solution of compound S4 (37.4 g, 0.136 mol) in acetic acid (110 ml) was subsequently added acetic anhydride (380 ml, 10 v/m) and sodium acetate (74g, 2 m/m). The resulting suspension was heated at reflux for 6 h. Then acetic anhydride and acetic acid were removed by vacuum concentration. The residue was cooled and poured in to water, subsequently extracted with ethyl acetate. The organic extracts were concentrated. To the residue in methanol was added 1N HCl (150 ml). The resulting suspension was heated at 100 °C for 2 h and concentratedthe resulting red precipitate was recovered by filtration, and dried at infrared to give white solid S5 (yield: 93percent). 1H-NMR (300MHzCDCl3): δ ppm 4.88 (s, 2H), 7.28 (d, J = 8.76 Hz, 1H), 7.79 (d, J = 2.01 Hz, 1H), 7.84 (dd, J = 8.76, 2.01 Hz, 1H).
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 15, p. 4537 - 4543
  • 2
  • [ 872191-29-2 ]
  • [ 54450-20-3 ]
YieldReaction ConditionsOperation in experiment
86.9% With hydrogenchloride In methanol; water Synthesis of 5-bromo-3(2H)-benzofuranone (Compound 4)
A mixture of Compound 3, methanol (10 mL), purified water (5 mL), and 1 N HCl (2 mL) was heated to reflux for 3 h under stirring.
After completion of the reaction, the reaction solution was cooled and purified water (100 ml) was added thereto.
The crystals formed were collected by vacuum filtration to give Compound 4. Yield: 0.50 g (yield rate: 86.9 percent) 1H NMR (300 MHz, CDCl3) d 4.67 (s, 2H), 7.06 (d, J = 9.0 Hz, 1H), 7.69 (dd, J = 2.1, 2.1 Hz, 1H), 7.79 (d, J = 2.1 Hz, 1H).
Reference: [1] Patent: EP2113258, 2009, A1,
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6354 - 6363
  • 3
  • [ 104-92-7 ]
  • [ 79-04-9 ]
  • [ 54450-20-3 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: With aluminum (III) chloride In dichloromethane at 25 - 40℃; for 78.75 h; Inert atmosphere
Stage #2: With sodium acetate In ethanol for 2 h; Reflux; Inert atmosphere
General procedure: To a solution of 1-fluoro-4-methoxybenzene (48, 10.0 mmol) indichloromethane (30 mL) was added chloroacetyl chloride(11.0 mmol) at 0 °C. After stirring for 15 min, the reaction mixturewas added anhydrous aluminium chloride (11.0 mmol) over 30 min. After stirring for 6 h at 40 °C, the reaction mixture was cool to rt. After stirring for 72 h at rt, the reaction mixture was poured into ice water (50 mL) and extracted with dichloromethane(3 30 mL). The combined organic phases were washed with brine,dried over anhydrous Na2SO4, and evaporated under vacuum without further purification. To a solution of the residue in ethanol(30 mL) was added anhydrous sodium acetate (20.0 mmol). After refluxing for 2 h, the reaction mixture was cooled to rt and concentrated under vacuum. The residue was dissolved in water (50 mL) and extracted with dichloromethane (3 40 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, and evaporated under vacuum. The crude mixture was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 40/1) to afford the title compound. Bright yellow solid, yield 60percent;
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 195 - 208
  • 4
  • [ 100959-21-5 ]
  • [ 54450-20-3 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 26, p. 8328 - 8332
[2] Patent: US2011/28414, 2011, A1, . Location in patent: Page/Page column 17
  • 5
  • [ 67029-74-7 ]
  • [ 54450-20-3 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 1, p. 17 - 20
  • 6
  • [ 106-41-2 ]
  • [ 54450-20-3 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 26, p. 8328 - 8332
  • 7
  • [ 104-92-7 ]
  • [ 54450-20-3 ]
Reference: [1] Patent: US2011/28414, 2011, A1,
  • 8
  • [ 2476-35-9 ]
  • [ 54450-20-3 ]
Reference: [1] Synlett, 2002, # 3, p. 501 - 503
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 1996, vol. 38, # 9, p. 863 - 871
  • 9
  • [ 62910-63-8 ]
  • [ 54450-20-3 ]
Reference: [1] Synlett, 2002, # 3, p. 501 - 503
  • 10
  • [ 7120-41-4 ]
  • [ 54450-20-3 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1996, vol. 38, # 9, p. 863 - 871
  • 11
  • [ 119-36-8 ]
  • [ 54450-20-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 15, p. 4537 - 4543
  • 12
  • [ 4068-76-2 ]
  • [ 54450-20-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 15, p. 4537 - 4543
  • 13
  • [ 186581-53-3 ]
  • [ 62910-63-8 ]
  • [ 54450-20-3 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1996, vol. 38, # 9, p. 863 - 871
  • 14
  • [ 867-13-0 ]
  • [ 54450-20-3 ]
  • [ 200204-85-9 ]
Reference: [1] Patent: US6127388, 2000, A,
  • 15
  • [ 54450-20-3 ]
  • [ 1099-45-2 ]
  • [ 200204-85-9 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 26, p. 8328 - 8332
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