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[ CAS No. 112968-89-5 ] {[proInfo.proName]}

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Chemical Structure| 112968-89-5
Chemical Structure| 112968-89-5
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CAS No. :112968-89-5 MDL No. :N/A
Formula : C11H15BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 275.14 Pubchem ID :-
Synonyms :

Safety of [ 112968-89-5 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 112968-89-5 ]

* 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.

  • Downstream synthetic route of [ 112968-89-5 ]

[ 112968-89-5 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 106-41-2 ]
  • [ 50586-80-6 ]
  • [ 112968-89-5 ]
Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 959 - 963
[2]Analytical Chemistry,1988,vol. 60,p. 901 - 905
  • 2
  • [ 80392-30-9 ]
  • [ 112968-89-5 ]
  • [ 929259-36-9 ]
Reference： [1]Tetrahedron,1988,vol. 44,p. 1553 - 1558
[2]Tetrahedron,1988,vol. 44,p. 1553 - 1558
[3]Tetrahedron,1988,vol. 44,p. 1553 - 1558
  • 3
  • [ 112968-89-5 ]
  • [ 106-95-6 ]
  • [ 112968-90-8 ]
Reference： [1]Analytical Chemistry,1988,vol. 60,p. 901 - 905
  • 4
  • [ 106-41-2 ]
  • [ 54149-17-6 ]
  • [ 112968-89-5 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; Example 36 Synthesis of N-{4-[2-(2-methoxyethoxy)ethoxy]phenyl}-17-methylmorphinan-3-amine (36), hydrochloride salt Step 1 : Potassium carbonate (839 mg, 6.07 mmol) was suspended in DMF (5 mL). 4-Bromophenol (350 mg, 2.023 mmol) and l-bromo-2-(2-methoxyethoxy)ethane (407 mg, 2.225 mmol) were added to the suspension. The mixture was stirred at 60 C overnight. The reaction mixture was poured into 20 mL of 5% LiCl solution and extracted with ethyl acetate (3 x 30 mL). The organic layer was washed with brine, was dried over sodium sulfate, was filtered and was concentrated. After drying under high vacuum, l-bromo-4-(2-(2- methoxyethoxy)ethoxy)benzene was obtained as colorless oil (537.9 mg) in 97% yield. H NMR (500 MHz, Chloroform-^/) delta 7.36 - 7.31 (m, 2H), 6.80 - 6.74 (m, 2H), 4.10 - 4.07 (m, 2H), 3.84 - 3.82 (m, 2H), 3.70 - 3.68 (m, 2H), 3.56 - 3.55 (m, 2H), 3.37 (s, 3H).
[0917] To a cooled (0 C.) suspension ofdry NaH (0.512 g,21.4 mmol) in anhydrous DMF (10 mL) under an Argonatmosphere, a solutionof4-bromophenol (3.11 g, 17.8mmol)in anhydrous DMF (20 mL) was added dropwise over 2-3min. The mixture was stirred at oo C. for 10 min and thenallowed to warm to rt over 30 min. To the resulting whitesuspension was added <strong>[54149-17-6]1-bromo-2-(2-methoxyethoxy)ethane</strong>(2.66 mL, 19.6 mmol) dropwise over 2 min and the mixturewas stirred at rt for 30 min and then at 65 C. for 1.5 h. Aftercooling to rt, the mixture was concentrated under reducedpressure to an oily suspension, diluted with brine (80 mL),and the mixture was extracted with EtOAc (3x60 mL). Thecombined extracts were washed with brine (2x25 mL), driedover Na2 S0 4 , filtered, and concentrated to give compound85a as a mobile, pale amber-colored oil, used inthe following reaction without further purification. Mass spectrum (LCMS,ESI pos.): Calcd. for C 11 H 15Br03 , 275.0/277.0 (M+H).found 275.2/277.1
Reference： [1]Patent: WO2016/182840,2016,A1 .Location in patent: Paragraph 00310
[2]Journal of Materials Chemistry C,2015,vol. 3,p. 9412 - 9424
[3]Bulletin of the Chemical Society of Japan,1997,vol. 70,p. 2519 - 2523
[4]Patent: US2014/364414,2014,A1 .Location in patent: Paragraph 0915-0917
  • 5
  • [ 112968-89-5 ]
  • dichloro-bis-{4-[2-(2-methoxy-ethoxy)-ethoxy]-phenyl}-silane [ No CAS ]
Reference： [1]Bulletin of the Chemical Society of Japan,1997,vol. 70,p. 2519 - 2523
  • 6
  • [ 112968-89-5 ]
  • tris{4-[2-(2-methoxyethoxy)ethoxy]phenyl}silane [ No CAS ]
Reference： [1]Bulletin of the Chemical Society of Japan,1997,vol. 70,p. 2519 - 2523
  • 7
  • [ 112968-89-5 ]
  • bis{4-[2-(2-methoxyethoxy)ethoxy]phenyl}silane [ No CAS ]
Reference： [1]Bulletin of the Chemical Society of Japan,1997,vol. 70,p. 2519 - 2523
  • 8
  • [ 111-77-3 ]
  • [ 112968-89-5 ]
Reference： [1]Analytical Chemistry,1988,vol. 60,p. 901 - 905
  • 9
  • [ 112968-89-5 ]
  • 4-bromo-N,N-bis(4-(2-(2-methoxyethoxy)ethoxy)phenyl)aniline [ No CAS ]
Reference： [1]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 1433 - 1439
  • 10
  • [ 112968-89-5 ]
  • 4-(5'-(5,5-dimethyl-1,3-dioxan-2-yl)-1,5'-bithiophen-2-yl)-N,N-bis(4-(2-(2-methoxyethoxy)ethoxy)phenyl)aniline [ No CAS ]
Reference： [1]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 1433 - 1439
  • 11
  • [ 112968-89-5 ]
  • 5'-(4-(bis(4-(2-(2-methoxyethoxy)ethoxy)phenyl)-amino)-phenyl)-2,2'-bithiophene-5-carbaldehyde [ No CAS ]
Reference： [1]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 1433 - 1439
  • 12
  • [ 112968-89-5 ]
  • (E)-3-(5'-(4-(bis(4-(2-(2-methoxyethoxy)ethoxy)phen-yl)-amino)phenyl)-2,2'-bithiophen-5-yl)-2-cyanoacrylic acid [ No CAS ]
Reference： [1]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 1433 - 1439
  • 13
  • [ 112968-89-5 ]
  • [ 62-53-3 ]
  • 4-(2-(2-methoxyethoxy)ethoxy)-N-(4-(2-(2-methoxyethoxy)ethoxy)phenyl)-N-phenylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.8% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 24h;Inert atmosphere; Reflux; A mixture of compound 1 (8.36 mmol, 2.30 g), aniline (3.80 mmol, 0.35 mL), Pd2(dba)3 (0.03 mol %, 0.15 g), P(t-Bu)3 (0.03 mol %,0.04 mL), and t-BuONa (12.49 mmol, 1.20 g) in dry toluene was refluxed for 24 h. After cooling, the solvent was evaporated. And the reaction mixture was poured into water and extracted with methylene chloride. The organic layerwas then dried over MgSO4 and the volatile organic solvent was removed using rotary evaporator. The pure product 2 was obtained by silica gel chromatography using a mixture of ethyl acetate and n-hexane (1:5) as an eluent (yield 90.8%). 1H NMR (300 MHz, Acetone-d6) delta 7.17 (t, J = 7.5Hz, 2H), 7.01 (d, J = 9.0 Hz, 4H), 6.93 (d, J = 9.0 Hz, 4H),6.87-6.85 (m, 3H), 4.10 (t, J = 4.5 Hz, 4H), 3.80 (t, J = 4.5Hz, 4H), 3.64 (t, J = 4.5 Hz, 4H), 3.50 (t, J = 4.2 Hz, 4H),3.29 (s, 6H). 13C NMR (75 MHz, Acetone-d6) delta 156.2,149.7, 141.9, 130.5, 127.3, 121.4, 121.3, 116.2, 72.6, 71.2,70.3, 68.5, 58.8. MS: m/z 481 [M+]. Anal. Calc. forC28H35NO6: C, 69.83; H, 7.33. Found: C, 69.44; H, 7.26.
Reference： [1]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 1433 - 1439
  • 14
  • [ 112968-89-5 ]
  • [ 73183-34-3 ]
  • 2-(4-(2-(2-methoxyethoxy)ethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 90℃; for 16h;Inert atmosphere; [0919] A mixture ofcompound 85a (2.00 g, 8.00 mmol),bis(pinacolato)diboron (2.49 g, 9.60 mmol), KOAc (2.35 g,24.0 mmol), and PdCI 2 ( dppf)-DCM (0.231 g, 0.280 mmol) inArgon-degassed DMSO (20 mL) was stirred at 90 C. underanArgon atmosphere for 16 h. After cooling tort, the reactionmixture was diluted with brine (200 mL) and extracted withEtOAc (3x50 mL). The combined extracts were washed withbrine (3x50 mL), dried over Na2 S04 , filtered, and concentrated to give give a dark brown oil which was purified byflash columnchromatography on silica gel (25-1 00% EtOAcheptane) to afford compound 85b as a colorless oil. Massspectrum (LCMS, ESI pos.): Calcd. for C 12H27B05 , 345.2(M+Na). found 345.2.
Reference： [1]Patent: US2014/364414,2014,A1 .Location in patent: Paragraph 0915; 0918-0919
  • 15
  • [ 112968-89-5 ]
  • 4-(5-(4-(2-(2-methoxyethoxy)ethoxy)phenyl)-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholine [ No CAS ]
Reference： [1]Patent: US2014/364414,2014,A1
  • 16
  • [ 112968-89-5 ]
  • (E)-4-(5-(4-(2-(2-methoxyethoxy)ethoxy)phenyl)-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholine [ No CAS ]
Reference： [1]Patent: US2014/364414,2014,A1
  • 17
  • [ 112968-89-5 ]
  • 2-(4,4''-bis(2-(2-methoxyethoxy)ethoxy)-[1,1':3',1''-terphenyl]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
Reference： [1]Journal of Materials Chemistry C,2015,vol. 3,p. 9412 - 9424
  • 18
  • [ 112968-89-5 ]
  • 1-bromo-3,5-bis{4-[2-(2-methoxyethoxy)ethoxy]phenyl}benzene [ No CAS ]
Reference： [1]Journal of Materials Chemistry C,2015,vol. 3,p. 9412 - 9424
  • 19
  • [ 61676-62-8 ]
  • [ 112968-89-5 ]
  • 2-(4-(2-(2-methoxyethoxy)ethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
Reference： [1]Journal of Materials Chemistry C,2015,vol. 3,p. 9412 - 9424
  • 20
  • C13H18BNO5 [ No CAS ]
  • [ 112968-89-5 ]
  • (4'-(2-(2-methoxyethoxy)ethoxy)-4-nitro-[1,1'-biphenyl]-3-yl)methanol [ No CAS ]
Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 959 - 963
  • 21
  • [ 112968-89-5 ]
  • [ 59946-91-7 ]
  • N-{4-[2-(2-methoxyethoxy)ethoxy]phenyl}-17-methylmorphinan-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 95℃; for 19h;Inert atmosphere; Step 2: A flask was charged with 17-methylmorphinan-3-amine (132.3 mg, 0.516 mmol) [Neumeyer et al. (2012) J Med Chem 55(8):3878-3890 and Zhang et al. (2004) J Med Chem 47(1): 165-174] and l-bromo-4-(2-(2-methoxyethoxy)ethoxy)benzene (151.1 mg, 0.549 mmol). Then, anhydrous toluene (12 mL) was added. Thereafter, a pre-mixed catalyst mixture of tns(dibenzylideneacetone)dipalladium(0):BINAP: sodium fert-butoxide (0.05:0.15:2) (124.3 mg) was added. The mixture was purged with nitrogen. The mixture was stirred at 95 oc for 19 hours. The mixture was cooled to room temperature, filtered and the solvent was removed. The residue was mixed with water, and then extracted with dichloromethane (3 x 25 mL). The combined organic solution was washed with brine, was dried over sodium sulfate, was filtered and was concentrated. The residue was purified by flash column chromatography on silica gel to result in 78.8 mg of product (36) as the free base in 29% yield. Tau NMR (500 MHz, Chloroform-c/) delta 6.97 - 6.93 (m, 3H), 6.84 - 6.82 (m, 3H), 6.73 (dd, J = 8.2, 2.1 Hz, 1H), 5.38 (s, 1H), 4.10 (t, J = 4.9 Hz, 2H), 3.83 (t, J = 5.0 Hz, 2H), 3.71 (dd, J = 5.5, 3.7 Hz, 2H), 3.57 - 3.56 (m, 2H), 3.38 (s, 3H), 2.94 (d, J = 18.1 Hz, 1H), 2.77 (br, 1H), 2.59 - 2.46 (m, 2H), 2.42- 2.40 (m, 1H), 2.38 (s, 3 H), 2.24 (d, J = 11.4 Hz, 1H), 2.13 - 2.08 (m, 1H), 1.78 (d, J = 12.5 Hz, 1H), 1.68 (m, 2H), 1.51 - 1.42 (m, 1H), 1.43 - 1.10 (m, 4H), 1.01 (m, 1H). MS for CjsHssNjOj: 451 (MH+). The free base was then dissolved in 1.5 mL of acetonitrile, followed by the addition of 3 mL of 1M hydrochloride to form the HC1 salt.
Reference： [1]Patent: WO2016/182840,2016,A1 .Location in patent: Paragraph 00311

Tags: 112968-89-5; 1-Bromo-4-(2-(2-methoxyethoxy)ethoxy)benzene;

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