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Product Details of [ 22385-77-9 ]

CAS No. :22385-77-9 MDL No. :MFCD00796945
Formula : C14H21Br Boiling Point : -
Linear Structure Formula :- InChI Key :BUOWTUULDKULFI-UHFFFAOYSA-N
M.W : 269.22 Pubchem ID :620136
Synonyms :

Safety of [ 22385-77-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
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Application In Synthesis of [ 22385-77-9 ]

* 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 [ 22385-77-9 ]
  • Downstream synthetic route of [ 22385-77-9 ]

[ 22385-77-9 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 22385-77-9 ]
  • [ 2380-36-1 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 34, p. 10354 - 10355
[2] Journal of the American Chemical Society, 2009, vol. 131, # 31, p. 11049 - 11061
  • 2
  • [ 124-38-9 ]
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  • [ 16225-26-6 ]
Reference: [1] Journal of Organometallic Chemistry, 1992, vol. 434, # 2, p. 151 - 158
  • 3
  • [ 22385-77-9 ]
  • [ 68-12-2 ]
  • [ 17610-00-3 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere
Stage #2: at 0℃; for 2.5 h;
Preparation 13 ,5-Di-/er/-butylbenzaldehydeDissolve l-bromo-3,5-di-/er/-butylbenzene (5.00 g, 18.57 mmol) in THF (50 mL) under a nitrogen atmosphere. Cool to -78 °C. Slowly add w-butyllithium (2.5 M in hexanes) (22.29 mL, 55.72 mmol) at -78 °C. Stir at -78 °C for about 30 min. Add DMF (4.31 mL, 55.72 mmol) dropwise. Warm the mixture to 0 °C and stir for 2.5 h. Pour aqueous NH4CI (30 mL) into the mixture. Extract with EtOAc (3 x 20 mL). Dry the combined organic portions over a2S04; filter; collect the filtrate; and concentrate under reduced pressure. Purify the residue using flash chromatography eluting with a gradient of 0-10percent EtO Ac/petroleum ether to afford the title compound (2.96 g, 73percent) as a white solid. LC-ES/MS m/z 219 [M+H]+.
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 13, p. 4710 - 4713
[2] Patent: WO2013/66640, 2013, A1, . Location in patent: Page/Page column 15
  • 4
  • [ 22385-77-9 ]
  • [ 2524-03-0 ]
  • [ 15181-11-0 ]
Reference: [1] Chemistry Letters, 2007, vol. 36, # 12, p. 1412 - 1413
  • 5
  • [ 1460-02-2 ]
  • [ 22385-77-9 ]
YieldReaction ConditionsOperation in experiment
68% With antimonypentachloride; bromine In dichloromethane at 0℃; for 5.25 h; Inert atmosphere; Darkness A dry, argon-flushed, 3-necked, 250 mL round-bottom flask was equipped with a condenser fitted with anitrogen gas inlet adapter, a thermometer, an addition funnel, and a Teflon-coated magnetic stir bar. 1,3,5-tri-tert-butyIbenzene (15.0 g, 61 mmol, 1.0 equiv) was added to 42 mL of dichloromethane under N2 withstirring and cooled to 0 °C. Using an argon-flushed syringe, 1.0 mL (7.8 mmol, 0.13 equiv) of SbCl5 wasadded. Liquid bromine (4.94 mL, 96.0 mmol, 1.6 equiv) was added to 20 mL CH2Cl2 and placed into theaddition funnel. The whole apparatus was wrapped in aluminum foil and placed in the dark. The Br2solution was added over 2 hours (approx. 1 drop per 2 sec). The solution was stirred for an additional 3hours at 0 °C and then poured into a mixture of 800 g ice and 800 mL water. The solution was stirred for15 min and approx. 100 mL of 5 M aqueous NaOH solution was added with stirring until alkaline (pH =8-9). Using a 2 L separatory funnel, the organic layer was extracted 3 times with CH2Cl2. The combinedorganic layers were then washed sequentially with water, saturated aqueous Na2S2O3 solution, water,brine, and then dried with MgSO4. The product was concentrated using the rotary evaporator and thenplaced under vacuum for several hours to dryness. The crude product was placed into a recrystallizationdish, 30 mL of hot ethanol was added, and the mixture was allowed to come to a boil using a hotplate.The dish was then cooled to RT and the solid mass filtered, washed 3 times with a minimum quantity ofcold ethanol, and then dried under vacuum, giving 11.1 g (68percent) of 1-bromo-3,5-di-tert-butylbenzene. 1HNMR (500 MHz, CDCl3): δ 1.30 (s, 18H), 7.17 (d, 1H), 7.32 (s, 2H). Analytical data matches thatreported in the literature.
Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 16, p. 4433 - 4451
[2] Synthetic Communications, 1996, vol. 26, # 9, p. 1693 - 1697
[3] Synlett, 2017, vol. 28, # 13, p. 1548 - 1553
[4] Organic Letters, 2005, vol. 7, # 24, p. 5365 - 5368
[5] Macromolecules, 2002, vol. 35, # 14, p. 5382 - 5387
[6] Journal of Organic Chemistry, 1995, vol. 60, # 8, p. 2411 - 2422
[7] Journal of the American Chemical Society, 1954, vol. 76, p. 2349,2351
[8] Canadian Journal of Chemistry, 1963, vol. 41, # 7, p. 1653 - 1656
[9] Journal of the American Chemical Society, 1968, vol. 90, p. 2115 - 2123
[10] Tetrahedron, 2015, vol. 71, # 2, p. 283 - 292
[11] Chemical Communications, 2015, vol. 51, # 10, p. 1926 - 1929
  • 6
  • [ 2380-36-1 ]
  • [ 22385-77-9 ]
Reference: [1] Canadian Journal of Chemistry, 2006, vol. 84, # 10, p. 1487 - 1503
[2] Recueil des Travaux Chimiques des Pays-Bas, 1956, vol. 75, p. 1327,1335
  • 7
  • [ 1460-02-2 ]
  • [ 4026-05-5 ]
  • [ 22385-77-9 ]
Reference: [1] Patent: EP1157047, 2003, B1,
  • 8
  • [ 1138-52-9 ]
  • [ 22385-77-9 ]
Reference: [1] Journal of the American Chemical Society, 1973, vol. 95, p. 8707 - 8713
  • 9
  • [ 1012-72-2 ]
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Reference: [1] Organic Preparations and Procedures International, 2000, vol. 32, # 2, p. 202 - 203
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 2349,2351
  • 10
  • [ 71-43-2 ]
  • [ 22385-77-9 ]
Reference: [1] Tetrahedron, 2015, vol. 71, # 2, p. 283 - 292
[2] Chemical Communications, 2015, vol. 51, # 10, p. 1926 - 1929
[3] Synlett, 2017, vol. 28, # 13, p. 1548 - 1553
  • 11
  • [ 16225-26-6 ]
  • [ 22385-77-9 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1956, vol. 75, p. 1327,1335
  • 12
  • [ 121-43-7 ]
  • [ 22385-77-9 ]
  • [ 197223-39-5 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.5 h;
Stage #2: at -78 - 20℃; for 14 h;
1-Bromo-3,5-di-t-butylbenzene and 40 mL of tetrahydrofuran were put in a 100-mL glass reactor, and cooled to −70° C. in a dry ice-heptane bath. 16.4 mL (40.9 mmol) of n-butyllithium-n-hexane solution (2.5 mol/L) was dropwise added thereto, and stirred for 30 minutes. Subsequently at −78° C., 4.25 g (40.9 mmol) of trimethyl borate was added and stirred for 2 hours, and further stirred at room temperature for 12 hours. An aqueous 1 M hydrogen chloride solution was added to the reaction liquid until the pH of the liquid could reach 3, then transferred into a separatory funnel, extracted three times with t-butyl methyl ether, and dried with sodium sulfate. Sodium sulfate was filtered away, the solvent was evaporated under reduced pressure, and the resultant crude product was purified through silica gel column chromatography (developing solvent, petroleum ether/ethyl acetate=20/1) to give 8.00 g (yield 91percent) of 3,5-di-t-butylphenylboronic acid as a pale yellow solid
Reference: [1] Patent: JP5710035, 2015, B2, . Location in patent: Paragraph 0169
[2] Chemical Communications, 2015, vol. 51, # 10, p. 1926 - 1929
[3] Chemistry - A European Journal, 2012, vol. 18, # 14, p. 4174 - 4178
[4] Patent: EP2532687, 2012, A2,
  • 13
  • [ 22385-77-9 ]
  • [ 197223-39-5 ]
Reference: [1] Journal of Chemical Sciences, 2011, vol. 123, # 5, p. 555 - 565
[2] Canadian Journal of Chemistry, 2006, vol. 84, # 10, p. 1487 - 1503
[3] Patent: US2009/30012, 2009, A1, . Location in patent: Page/Page column 23
[4] Chemical Communications, 2011, vol. 47, # 26, p. 7341 - 7343
  • 14
  • [ 5419-55-6 ]
  • [ 22385-77-9 ]
  • [ 197223-39-5 ]
Reference: [1] Synlett, 2017, vol. 28, # 14, p. 1775 - 1779
  • 15
  • [ 22385-77-9 ]
  • [ 197223-39-5 ]
Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 16, p. 4433 - 4451
  • 16
  • [ 22385-77-9 ]
  • [ 1433497-19-8 ]
Reference: [1] Patent: WO2013/66640, 2013, A1,
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