Home Cart 0 Sign in  

[ CAS No. 377091-18-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 377091-18-4
Chemical Structure| 377091-18-4
Structure of 377091-18-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 377091-18-4 ]

Related Doc. of [ 377091-18-4 ]

Alternatived Products of [ 377091-18-4 ]

Product Details of [ 377091-18-4 ]

CAS No. :377091-18-4 MDL No. :MFCD09864851
Formula : C8H7Br3O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 358.85 Pubchem ID :-
Synonyms :

Safety of [ 377091-18-4 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 377091-18-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 377091-18-4 ]
  • Downstream synthetic route of [ 377091-18-4 ]

[ 377091-18-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 377091-18-4 ]
  • [ 66826-78-6 ]
Reference: [1] Organic Letters, 2001, vol. 3, # 21, p. 3357 - 3360
  • 2
  • [ 377091-18-4 ]
  • [ 189035-22-1 ]
YieldReaction ConditionsOperation in experiment
94% With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 4 h; nBuLi (2.5 M in hexane, 5.13 ml_, 12.84 mmol) was added to a -78°C cooled solution of 1 ,4-dibromo-2-(2-bronnoethoxy)benzene (3.84 g, 10.70 mmol) in THF (100 ml_). The reaction mixture was stirred at low temperature for 4 h. It was poured into H2O (100 ml_) and extracted with EtOAc (2x100 ml_). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was purified by flash chromatography on SiO2 (3percentEtOAc/hexanes) to furnish 6-bromo-2,3-dihydro-1-benzofuran (2. g, yellow solid, yield: 94percent).
85% With n-butyllithium In tetrahydrofuran; benzene at -78℃; for 1 h; Inert atmosphere To a solution of 1,4-dibromo-2-(2-bromoethoxy) benzene (2.13 g, 5.9 mmol) in benzene / tetrahydrofuran (28 mL, 2:5) at -78°C under N2 was added n-butyllithium (2.5 mL, 6.1 mmol). The mixture was stirred at -78°C for 1 h, and quenched by acetic acid. Water was added, and the organic layer was seperated, dried, and concentrated under vacuum to give the title compound (1.00 g, 85 percent). 1H NMR (CDCl3): δ 7.03 (1H, d, J = 8.0 Hz), 6.91-6.93 (2H, m), 4.58 (2H, t, J = 4.8 Hz), 3.15 (2H, t, J = 4.8 Hz)
85% With n-butyllithium In tetrahydrofuran; benzene at -78℃; for 1 h; Inert atmosphere To a solution of 1,4-dibromo-2-(2-bromoethoxy) benzene (2.13 g, 5.9 mmol) in benzene/ tetrahydrofuran (28 mL, 2:5) at −78° C. under N2 was added n-butyllithium (2.5 mL, 6.1 mmol). The mixture was stirred at −78° C. for 1 h, and quenched by acetic acid. Water was added, and the organic layer was seperated, dried, and concentrated under vacuum to give the title compound (1.00 g, 85percent). 1H NMR (CDCl3) δ7.03 (1H, d, J=8,0 Hz), 6.91-6.93 (2H, m), 4.58 (2H, t, J=4.8 Hz), 3.15 (2H, t, J=4.8 Hz).
79% With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 2.5 h; Inert atmosphere 1.6 M n-Butyllithium/hexane solution (21.84 mL, 34.94 mmol) was slowly added to a solution of 1,4-dibromo-2-(2-bromoethoxy)benzene (10.45 g, 29.12 mmol) in THF (200 mL) at-78°C under argon gas atmosphere. The reaction mixture was stirred at -78°C for 30 min, and then at 0°C for 2 hr. The reaction mixture was added to ice water, and 2N hydrochloric acid was added thereto until the pH of the mixture became 3. Then, the mixture was extracted three times with a mixed solvent of ethyl acetate/hexane (3:1). The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 2→8percent ethyl acetate/hexane) to give 6-bromo-2,3-dihydrobenzofuran (4.57 g, 22.96 mmol, 79percent) as a white solid.
9.4 g With n-butyllithium In tetrahydrofuran; hexaneInert atmosphere; Cooling To a solution of 1,4-dibromo-2-(2-bromoethoxy)benzene (22.3 g, 62.2 mmol) in THF (180 mL) was added 1.57 M n-BuLi in hexanes (40 mL, 62.8 mmol) under Ar at -76 °C.
After stirring at -76 °C overnight, the mixture was quenched with sat.
NH4Cl aq and extracted with AcOEt.
The organic phase was washed with brine and dried over Na2SO4.
After filtration and evaporation, the residue was recrystallized from ethanol (28 mL) and water (3 mL) to obtain 7 as a white solid (9.4 g, 76percent).
1H NMR (400 MHz, CDCl3) δ = 7.03 (d, J = 7.6 Hz, 1H), 6.97 (d, J = 1.6 Hz, 1H), 6.94 (dd, J = 1.6, 7.6 Hz, 1H), 4.59 (t, J = 8.8 Hz, 2H), 3.15 (t, J = 8.8 Hz, 1H); MS (ESI+) 200.1 (M+H)+.

Reference: [1] Patent: WO2009/7399, 2009, A1, . Location in patent: Page/Page column 86
[2] Patent: EP2862571, 2015, A1, . Location in patent: Paragraph 0146; 0147
[3] Patent: US2015/166559, 2015, A1, . Location in patent: Paragraph 0200; 0201
[4] Patent: TW2016/2105, 2016, A, . Location in patent: Paragraph 1108
[5] Patent: US2010/16297, 2010, A1, . Location in patent: Page/Page column 34
[6] Patent: US2011/263612, 2011, A1, . Location in patent: Page/Page column 165
[7] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4792 - 4803
  • 3
  • [ 377091-18-4 ]
  • [ 1083168-69-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4792 - 4803
Same Skeleton Products
Historical Records