* 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
3
[ 608-33-3 ]
[ 74-88-4 ]
[ 38603-09-7 ]
Yield
Reaction Conditions
Operation in experiment
98%
Stage #1: With potassium carbonate In acetone at 20℃; for 0.5 h; Stage #2: at 60℃; for 3 h;
Example 1 Preparation of 2,6-Dibromo-4-(6-(3-bromobenzyloxy)pyridazin-3-yl)phenol (compound 91) To a stirred solution of 2,6-dibromophenol (5.26 g, 20.9 mmol) in acetone (170 mL) was added anhydrous potassium carbonate (4.33 g, 31.3 mmol) and the mixture was stirred at room temperature for 30 min. Iodomethane (1.97 mL, 31.4 mmol) was then added and the mixture was heated at 60° C. for 3 h. The mixture was filtered and the filtrate was evaporated. The residue was partitioned between petroleum ether (40-60° C., 100 mL) and water (100 mL). The aqueous layer was further extracted with petroleum ether (40-60° C., 100 mL) and the combined organic extracts were washed with brine (50 mL), dried (MgSO4) and evaporated to leave 5.43 g (98percent) of the title compound as a colorless oil. 1H NMR δ (ppm)(CDCl3): 3.89 (3H, s), 6.86 (1H, t, J=8.02 Hz), 7.50 (2H, d, J=8.01 Hz).
92%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere Stage #2: at 20℃;
21.2) 2,6-dibromo-methoxy-benzene (intermediate 66); To a solution of 2,6-dibromo-phenol (30 g, 119.09 mmol) in DMF (160 ml) at O0C was added NaH (60percent, 5.72 g, 142.91 mmol) portionwise under argon. After 30 min methyl iodide (7.78 ml, 125.05 mmol) was added dropwise and the reaction mixture was stirred for 4 h at RT. The mixture was diluted with ethyl acetate (100 ml), washed with water (2x 200 ml) and brine (100 ml), dried over Na2SO4, and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel (eluent: AcOEt/cyclohexane 1/4). Yield: 29.08 g, 92 percent
Reference：
[1] Tetrahedron Letters, 2008, vol. 49, # 33, p. 4912 - 4914
[2] Patent: US2009/270398, 2009, A1, . Location in patent: Page/Page column 35
[3] Journal of the American Chemical Society, 2009, vol. 131, # 47, p. 17371 - 17375
[4] Journal of the American Chemical Society, 2016, vol. 138, # 31, p. 9779 - 9782
[5] Patent: WO2009/103440, 2009, A1, . Location in patent: Page/Page column 75
[6] Journal of the American Chemical Society, 2011, vol. 133, # 34, p. 13317 - 13319
[7] Advanced Synthesis and Catalysis, 2008, vol. 350, # 13, p. 2024 - 2032
4
[ 608-33-3 ]
[ 38603-09-7 ]
Yield
Reaction Conditions
Operation in experiment
96%
With potassium carbonate; dimethyl sulfate In n-heptane; ethyl acetate; acetonitrile
2,6-Dibromoanisole (1): A mixture of 2,6-dibromophenol (25 g, 0.099 mol), powder potassium carbonate (28 g, 0.2 mol, 2 equiv) and dimethyl sulfate (12.6 g, 0.099 mol) in acetonitrile (400 mL) was kept at reflux with good stirring for 4 hr. After cooling, the solids were removed by filtration and the solvent was removed in a rotary evaporator. The residue was taken in 2:1 heptane/ethyl acetate mixture (800 mL) and washed with water (2*400 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was removed in a rotary evaporator, leaving almost pure 1 (15.5 g, 96percent).
Reference：
[1] Patent: US2011/98425, 2011, A1,
[2] Journal of Applied Chemistry, 1956, vol. 6, p. 125,126
5
[ 608-33-3 ]
[ 77-78-1 ]
[ 38603-09-7 ]
Reference：
[1] Journal of the American Chemical Society, 1932, vol. 54, p. 1465,1468
[2] Journal of Organic Chemistry, 1966, vol. 31, p. 3666 - 3671
3,3-Dimethylbut-l-yne (1.6 g, 20 mmol) was added to a solution of 2,6- dibromophenol (5.0 g, 20 mmol) and Cu2O (1.7 g, 12 mmol) in dry pyridine (50 mL) under N2, then the mixture was heated to about 55 0C and stirred overnight. The mixture was filtered and the filtrate was concentrated to give a residue, which was dissolved in EtOAc. This solution was washed with brine and dried over Na2SO4. The solvent was removed and the residue was purified by column chromatography to afford 7-brorno-2-tert-butyl-benzofuran (1.3 g, 26%). 1H NMR (CDCl3): 1.40(S, 9H)3 6.41(s, IH), 7.04(1, IH), 7.38(d, IH), 7.42(d, IH).
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;
A solution comprising <strong>[608-33-3]2,6-dibromophenol</strong> (3.90g, 15.00mmol), potassium carbonate (2.48g, 17.94mmol) and DMF (40nl) was added with 1-bromo-2-chloro ethane (4.30g, 29.98mmol) and stirred at room temperature for 16 hours. The reaction solution was concentrated and liquid separation was carried out with ethyl acetate-water. The organic layer was washed with saturated sodium chloride water and dried with anhydrous sodium sulfate. The residue obtained by concentration was purified by silica gel column chromatography (n-hexane) to obtain the target compound (4.75g, quant.) as a colorless oily substance. 1H-NMR (300MHz, CDCl3) delta=3.91 (2H, t, J=6.6Hz), 4.27 (2H, t, J=6.6Hz), 6.89 (1H, t, J=7.8Hz), 7.51 (2H, d, J=7.8Hz).
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