* 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.
Reference:
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2617 - 2625
2
[ 106-48-9 ]
[ 695-96-5 ]
[ 5324-13-0 ]
Reference:
[1] RSC Advances, 2018, vol. 8, # 32, p. 17806 - 17812
[2] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
[3] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
[4] Tetrahedron, 2007, vol. 63, # 23, p. 4959 - 4967
[5] Tetrahedron, 2007, vol. 63, # 23, p. 4959 - 4967
3
[ 5324-13-0 ]
[ 695-96-5 ]
Reference:
[1] Journal of Organic Chemistry, 1946, vol. 11, p. 641,644
4
[ 106-48-9 ]
[ 5324-13-0 ]
Reference:
[1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3373 - 3375
[2] Synlett, 2011, # 15, p. 2265 - 2269
[3] Journal of the American Chemical Society, 1917, vol. 39, p. 2643
[4] Monatshefte fuer Chemie, 1925, vol. 46, p. 107
[5] Polish Journal of Chemistry, 1994, vol. 68, # 3, p. 453 - 458
[6] Russian Journal of Applied Chemistry, 2000, vol. 73, # 9, p. 1526 - 1530
[7] Tetrahedron, 2007, vol. 63, # 23, p. 4959 - 4967
5
[ 1679-18-1 ]
[ 5324-13-0 ]
Reference:
[1] Advanced Synthesis and Catalysis, 2009, vol. 351, # 10, p. 1567 - 1574
6
[ 106-48-9 ]
[ 695-96-5 ]
[ 5324-13-0 ]
Reference:
[1] RSC Advances, 2018, vol. 8, # 32, p. 17806 - 17812
[2] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
[3] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
[4] Tetrahedron, 2007, vol. 63, # 23, p. 4959 - 4967
[5] Tetrahedron, 2007, vol. 63, # 23, p. 4959 - 4967
7
[ 106-47-8 ]
[ 106-39-8 ]
[ 5324-13-0 ]
Reference:
[1] Journal of the American Chemical Society, 1947, vol. 69, p. 1221
8
[ 7726-95-6 ]
[ 64-19-7 ]
[ 106-48-9 ]
[ 5324-13-0 ]
Reference:
[1] Journal of the American Chemical Society, 1917, vol. 39, p. 2643
With ammonium peroxodisulfate; sodium bromide; In water; at 20℃; for 6h;Irradiation;
General procedure: 1 mmol of phenol was added to a photocatalytic reactor,5.0 mmol sodium bromide, 0.2 mmol amine persulfate, 3 mL water, at room temperature,The reaction was performed in a photocatalytic reactor at 5W for 6 hours.After the reaction was completed, it was extracted with a small amount of ethyl acetate, and the organic phase was recrystallized.A white solid was obtained with a yield of 83%.
trimethylsilyl 2,6-dibromo-4-chlorophenyl ether[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
98%
With triethylamine; In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere;
General procedure: An oven dried flask was charged with 2-bromophenol (1.0equiv) and capped with an inlet adapter with a 3-way stopcockand then evacuated and back-filled with argon. AnhydrousTHF (0.10-0.50 M), Et3N (1.5 equiv) and Me3SiCl (1.5 equiv)were added via syringes and the reaction mixture was stirredfor a few hours at room temperature. The reaction mixturewas concentrated under reduced pressure. Hexane was addedto the residue and the mixture was filtered through a silica gelpad and washed with hexane. The solution was evaporated togive 2-bromophenyl trimethylsilyl ether. Without purificationof the obtained material, anhydrous THF (0.10-0.33 M) wasadded to the flask and the mixture was cooled to -78C. n-BuLi (1.6 M hexane solution, 1.2 equiv) was added dropwise at-78C and the reaction was allowed to warm up to room temperatureand stirred for several hours. To the reaction mixturewas added a saturated aqueous solution of NH4Cl for quenching.The mixture was extracted with EtOAc (this process wasrepeated three times) and combined organic phase was driedover anhydrous Na2SO4. The organic phase was filtered andconcentrated under reduced pressure. The residue was purifiedby flash column chromatography on silica gel (hexane/EtOAc)to provide 2-(trimethylsilyl) phenol 2.
3,5-cis-bis(2,6-dibromo-4-chlorophenoxy)cyclopent-1-ene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
55%
Sodium hydride (7.7 g, 0.32 mol) was added to a solution of <strong>[5324-13-0]2,6-dibromo-4-chlorophenol</strong> (50.0 g, 0.17 mol) in dry N,N-dimethylformamide (300 mL). The mixture was stirred for 0.5 h at 0C. Then 3,5-cis-dibromocyclopent-1-ene (19.7 g, 87 mmol) was added dropwise to the mixture at 0C which was stirred for 2 h. The mixture was poured into saturated sodium bicarbonate (700 mL) and filtered. The crude product was collected and ovendried. Dichloromethane (500 mL) was added to the crude product and the mixture was stirred for 1 h. Then the mixture was filtered. The filtrate was evaporated to dryness and purified by flash column chromatography (dichloromethane/petroleum ether, 1:2) to give the pure compound 3 as a colourless solid: Yield 61.2 g (55%); m.p. 165.5-167.5C; 1H NMR (400 MHz, CDCl3): 2.72 (s, 2H), 5.67 (s, 2H), 6.32 (s, 2H), 7.56 (s, 4H); 13C NMR (100 MHz, CDCl3): 152.0, 136.2, 132.5, 130.2, 118.8, 88.5, 39.0; IR (KBr) 1570, 1530, 1440, 820, 735 cm-1. Anal. calcd for C17H10Br4Cl2O2: C, 32.07; H, 1.58; found: C, 32.05; H, 1.61%.