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Chemical Structure| 90-11-9
Chemical Structure| 90-11-9
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Product Details of [ 90-11-9 ]

CAS No. :90-11-9 MDL No. :MFCD00003868
Formula : C10H7Br Boiling Point : -
Linear Structure Formula :- InChI Key :DLKQHBOKULLWDQ-UHFFFAOYSA-N
M.W : 207.07 Pubchem ID :7001
Synonyms :

Calculated chemistry of [ 90-11-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.65
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 3.62
Log Po/w (WLOGP) : 3.6
Log Po/w (MLOGP) : 4.05
Log Po/w (SILICOS-IT) : 3.7
Consensus Log Po/w : 3.47

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.08
Solubility : 0.0173 mg/ml ; 0.0000837 mol/l
Class : Moderately soluble
Log S (Ali) : -3.31
Solubility : 0.102 mg/ml ; 0.000492 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.93
Solubility : 0.00243 mg/ml ; 0.0000117 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.28

Safety of [ 90-11-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 90-11-9 ]

* 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 [ 90-11-9 ]
  • Downstream synthetic route of [ 90-11-9 ]

[ 90-11-9 ] Synthesis Path-Upstream   1~43

  • 1
  • [ 90-11-9 ]
  • [ 75-36-5 ]
  • [ 46258-62-2 ]
YieldReaction ConditionsOperation in experiment
91% With aluminum (III) chloride In 1,2-dichloro-ethane at 0 - 20℃; for 24 h; A solution of 1-Bromo-naphthalene (10 g, 48.3 mmol) and acetyl chloride (4.2 ml, 58 mmol) in 1,2-dichloroethane (100 ml) was cooled to 0°C and aluminum chloride (14.4 g, 108 mmol) was added portion wise. The mixture was stirred at RT for 24 hours. The reaction mixture was poured into ice-water (100 ml). The two layers were separated and the water layer was extracted with diethyl ether (3 x 150 ml). The combined organic layers were dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure to give an orange colored oil. The 1- (4-bromo-naphtalen-1-yl)-ethanone was purified by flash chromatography (cyclohexane/ethylacetate: 95/5), yielding an yellow oil (91percent yield). The 1- (4-bromo-naphtalen-1-yl)-ethanone oxime was prepared according to the procedure described for Compound 22, yielding a white powder (98percent yield). Activated zinc dust (24.7 g, 379 mmol) was added portion wise to a suspension of the oxime (10.0 g, 37.9 mmol) in acetic acid (40 ml). The mixture was stirred at RT for 2 hours. The zinc dust was removed by filtration and acetic acid was removed under reduced pressure. Water (100 ml) was added and the pH was adjusted to pH = 13 with 1N NaOH. The water layer was extracted with EtOAc (3 x 100 ml). The combined organic layers were dried over MgS04, filtered and the solvent was removed under reduced pressure, yielding a yellow oil (70percent yield). Boc20 (7.1 g, 31.8 mmol) was added to a solution of the amine (6.6 g, 26.5 mmol) in 1,4-dioxane (50 ml). The reaction mixture was stirred at RT for 2 hours. The solvent was removed under reduced pressure and the product was purified by flash chromatography (cyclohexane/EtOAc: 95/5), yielding a yellow powder (75percent yield). The bromide (350 mg, 1 mmol) was dissolved in THF (13 ml) /water (2 ml). Potassium acetate (100 mg, 1 mmol), 1,3-bis-diphenylphosphinopropane (9.0 mg, 0.02 mmol) and palladium- (11)-acetate (9.0 mg, 0.04 mmol) were added. The mixture was stirred at 50 atm CO pressure and 150°C for 3 hours. The reaction mixture was filtered, the filtrate dried over MgS04 and the solvent was removed under reduced pressure to give a yellow- greenish oil (300 mg). The 4- (l-tert-butoxycarbonylamino-ethyl)-naphthalene-l- carboxylic acid was purified by flash chromatography (DCM/MeOH : 90/10), yielding a white powder (14percent yield). The title product was prepared according to the procedure of Compound 31, starting from 4- (1-tert-butoxycarbonylamino-ethyl)-naphthalene-1-carboxylic acid (44 mg) and 4-amino-pyridine (67percent yield).'H NMR (300 MHz, , DMSO-d6): 1.64 ppm (d, 3H, J = 6.6 Hz); 5.3 ppm (q, 1H, J = 6.5 Hz), 7.71 ppm (m, 1H), 8.00 ppm (d, 1H, J = 7.7 Hz), 8.32 ppm (m, 1H), 8. 35 ppm (d, 1H, J = 7.3 Hz), 8.81 ppm (d, 2H, J = 7.2 Hz), 12.2 ppm (s, 1H).
91% at 0 - 20℃; for 24 h; Section IExample I-IPreparation of Compound 301 and 302General Procedure I-AA solution of 1-Bromo-naphthalene (I-Ia; 2 g, 9.6 mmol) and acetyl chloride (0.84 mL, 11.6 mmol) in 1,2-dichloroethane (30 mL) was cooled to 0° C. and aluminum chloride (2.88 g, 21.6 mmol) was added portion wise. The mixture was stirred at r.t. for 24 hours. The reaction mixture was poured into ice-water (100 mL). The two layers were separated and the aqueous layer was extracted with EtOAc (150 mL.x.3). The combined organic layers were dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure to give compound I-Ib as an orange oil (2.16 g, yield 91percent). 1H NMR (400 MHz, CDCl3) δ 8.6 (m, 1H), 8.3 (m, 1H), 7.8 (d, J=8.0 Hz, 1H), 7.66 (d, J=7.6 Hz, 1H), 7.58 (m, 2H), 2.63 (s, 3H). MS (ESI) m/z (M+H)+ 250.
62% With aluminum (III) chloride In carbon disulfide at 0 - 20℃; for 120 h; Inert atmosphere To a stirred solution of 1.00 g (4.8 mmol) of 1-bromonaphthalene in 15 mL of carbon disulfide at 0 °C in a flame-dried flask under N2 was added 0.42 g (5.3 mmol) of acetyl chloride. This solution was stirred at 0 °C for 10 min and 0.84 g (6.3 mmol) of AlCl3 was added. The reaction was stirred at 0 °C for 3 days followed by 2 days of stirring at ambient temperature. The reaction mixture was poured over ice and concentrated HCl, extracted with ether, washed with NaHCO3 and brine. After drying (MgSO4) the solution was concentrated in vacuo and purified by chromatography (petroleum ether/ether, 95:5) to give 0.75 g (62percent) of 1-acetyl-4-bromonaphthalene as a brown oil: 1H NMR (300 MHz, CDCl3) δ 2.74 (s, 3H), 7.65-7.69 (m, 2H), 7.74 (d, J = 6 Hz, 1H), 7.83 (d, J = 6 Hz, 1H), 8.32-8.35 (m, 1H), 8.72-8.75 (m, 1H); 13C NMR (75.5 MHz, CDCl3) δ 30.1, 126.4, 127.5, 127.8, 128.2, 128.4, 128.7, 128.7, 131.2, 132.3, 135.2, 201.0; GC/MS (EI) m/z (rel intensity) 248 (46), 233 (100), 205 (44). The data agree in all respects with those reported previously.
Reference: [1] Patent: WO2005/82367, 2005, A1, . Location in patent: Page/Page column 64-65
[2] Patent: US2011/152246, 2011, A1, . Location in patent: Page/Page column 110; 111
[3] Canadian Journal of Chemistry, 1981, vol. 59, p. 2629 - 2641
[4] Canadian Journal of Chemistry, 1995, vol. 73, # 6, p. 885 - 895
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 6, p. 2067 - 2081
[6] Chemische Berichte, 1891, vol. 24, p. 550
[7] Journal of Organic Chemistry, 1946, vol. 11, p. 27,30
[8] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1931, vol. <A>, p. 59,65
[9] Journal of Organic Chemistry, 2005, vol. 70, # 22, p. 9036 - 9039
  • 2
  • [ 90-11-9 ]
  • [ 108-24-7 ]
  • [ 46258-62-2 ]
Reference: [1] Israel Journal of Chemistry, 1963, vol. 1, p. 1 - 11
  • 3
  • [ 75-15-0 ]
  • [ 7446-70-0 ]
  • [ 90-11-9 ]
  • [ 75-36-5 ]
  • [ 46258-62-2 ]
Reference: [1] Journal of Organic Chemistry, 1946, vol. 11, p. 27,30
[2] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1931, vol. <A>, p. 59,65
  • 4
  • [ 201230-82-2 ]
  • [ 90-11-9 ]
  • [ 879-18-5 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9550 - 9555
  • 5
  • [ 90-11-9 ]
  • [ 86-74-8 ]
  • [ 22034-43-1 ]
YieldReaction ConditionsOperation in experiment
75% With copper(l) iodide; 18-crown-6 ether; potassium carbonate In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) at 170 - 180℃; for 13.5 h; [Embodiment 8]; [0397]In this embodiment, a synthetic method of2-{iV-(l-naphthyl)-iV-[9-(l-naphthyl)carbazol-3-yl]ammo}-9,10-diphenylanthracene (abbreviation: 2NCNPA), which is the anthracene derivative of the present invention represented by Structural Formula (220), is specifically described. ; [0398] <n="170"/>[0399][Step 1] Synthesis of N^-d^l-naphthyl^H-carbazole-S-amine (abbreviation: NCN)[0400](i) Synthesis of 9-(l-naphthyl)carbazole.A synthetic scheme of 9-(l-naphthyl)carbazole is shown in (C-18). [0401]CuI, 18-crown-6-ether, K2CO3, DMPU (C-18)[0402] 21 g (0.1 mol) of 1-bromonaphthalene, 17 g (0.1 mol) of carbazole, 950 mg (5 mmol) of copper iodide (I), 33 g (240 mmol) of potassium carbonate, and 660 mg (2.5 mmol) of 18-crown-6-ether were put into a 500 mL three-neck flask, and nitrogen substitution was carried out in the flask. To this mixture was added 80 mL of l,3-dimethyl-3,4,5,6-tetrahydro-2(l/-T)-pyrimidinone (abbreviation: DMPU), which was <n="171"/>followed by stirring for 6 hours at 170 0C under nitrogen. To this reaction mixture was further added 10 g (50 mmol) of 1-bromonaphthalene, 2.0 g (10 mmol) of copper iodide (I), and 2.6 g (10 mmol) of 18-crown-6-ether, and stirring was further conducted for 7.5 hours at 170 0C. Furthermore, to this reaction mixture was added 10 g (50 mmol) of 1-bromonaphthalene, and additional stirring was carried out for 6 hours at 1800C. After the reaction was completed, to this reaction mixture was added about 200 mL of toluene and about 100 mL of 1 mol/L hydrochloric acid, and then the mixture was filtered through celite. The obtained filtrate was filtered through Florisil and celite. The obtained filtrate was separated into an organic layer and an aqueous layer, and after this organic layer was washed with 1 mol/L hydrochloric acid and then with water, the organic layer was dried over magnesium sulfate. This suspension was filtered through Florisil and celite. The filtrate was concentrated to give an oily -substrate, and methanol was added to this oily substrate, followed by irradiation with ultrasound to precipitate a solid. The solid precipitated was collected by suction filtration, giving 22 g of 9-(l-naphthyl)carbazole as white powder (75percent yield). The Rf values (SiO2, eluent; hexane:ethyl acetate = 10:1) of 9-(l-naphthyl)carbazole, 1-bromonaphthalene, and carbazole were 0.61, 0.74, and 0.24, respectively.
75% With 18-crown-6 ether; potassium carbonate In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 170 - 180℃; for 19.5 h; Step 1: Synthesis of 9-(l-naphthyl)-9H-carbazole][0700]A synthetic scheme of 9-(l-naphthyl)-9H-carbazole in Step 1 is shown in the following (R-I). [0701][0702]In a 500-mL three-neck flask, 21 g (100 mmol) of 1-bromonaphthalene, 17 g (100 mmol) of carabazole, 0.1 g (5.0 mmol) of copper(I) iodide, 0.7 g (2.5 mmol) of 18-crown-6-ether, 33 g (240 mmol) of potassium carbonate, and 80 mL of l,3-dimethyl-3,4,5,6-tetrahydro-2(lH)pyrimidinone (abbreviation: DMPU) were put, <n="239"/>and the mixture was stirred under a nitrogen atmosphere at 170 0C for 6 hours. Then, 10 g (50 mmol) of 1-bromonaphthalene, 2.0 g (10 mmol) of copper(I) iodide, and 2.6 g (10 mmol) of 18-crown-6-ether were further added to this reaction mixture, and the mixture was further stirred at 170 0C for 7.5 hours. After that, 10 g (50 mmol) of 1-bromonaphthalene was further added to this reaction mixture, and the mixture was further stirred at 180 0C for 6 hours. [0703]After the reaction, about 200 mL of toluene and about 100 mL of hydrochloric acid (1 mol/L) were added to this reaction mixture, and the mixture was filtered through Celite. The obtained filtrate was filtrated through Florisil and Celite. The obtained filtrate was separated into an organic layer and an aqueous layer. After this organic layer was washed with hydrochloric acid (1 mol/L) and water in this order, magnesium sulfate was added to remove moisture. This suspension was filtered through Florisil and Celite. Then, hexane was added to the oily substance obtained by concentrating the obtained filtrate, and the mixture was irradiated with supersonic and then recrystallized to obtain 22 g of an objective white powder at a yield of 75 percent.
Reference: [1] Patent: WO2007/125934, 2007, A1, . Location in patent: Page/Page column 168-169
[2] Patent: WO2009/72587, 2009, A1, . Location in patent: Page/Page column 237-238
[3] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2006, vol. 63, # 1, p. 15 - 20
[4] Journal of Organic Chemistry, 2009, vol. 74, # 9, p. 3341 - 3349
  • 6
  • [ 623-03-0 ]
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  • [ 1413355-67-5 ]
  • [ 22034-43-1 ]
  • [ 57103-17-0 ]
Reference: [1] Science, 2012, vol. 338, # 6107, p. 647 - 651
  • 7
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  • [ 6627-78-7 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 33, p. 8609 - 8613
  • 8
  • [ 90-11-9 ]
  • [ 523-27-3 ]
  • [ 26979-27-1 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 11, p. 4326 - 4329
  • 9
  • [ 90-11-9 ]
  • [ 90-14-2 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere
Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 20℃; for 0.25 h; Inert atmosphere
General procedure: Aryl bromide (10 mmol) was dissolved in dry THF (30 mL) and cooled to -78 °C under anargon atmosphere. n-Butyllithium (1.6 M in n-hexane; 7.5 mL; 12 mmol) was addeddropwise. After 15 minutes a solution of I2 (3.81 g; 15 mmol) in dry THF (10 mL) was addedand the reaction mixture was allowed to warm to room temperature overnight.For workup the reaction mixture was concentrated in vacuo. H2O was added to the residueand it was extracted with DCM (3x). The combined organic phases were washed withsaturated Na2S2O5 solution and H2O. After drying over MgSO4 and concentration underreduced pressure, the crude product was purified by column chromatography.
92 %Chromat. With copper(I) oxide; <i>L</i>-proline; potassium iodide In ethanol at 110℃; for 30 h; Schlenk technique; Inert atmosphere; Sealed tube General procedure: A Schlenk tube was charged with Cu2O (7.2 mg, 10 molpercent), l-proline (11.5 mg, 20 molpercent), aryl (or heteroaryl) bromide (1 or 3,0.50 mmol), potassium iodide (KI) (249 mg, 0.75 mmol), and EtOH(1.5 mL) under nitrogen atmosphere. The Schlenk tube was sealedwith a teflon valve, and then the reaction mixture was stirred at110C for a period (the reaction progress was monitored by GCanalysis). After the reaction was completed, GC yield of high volatileproduct was determined using an appropriate internal standard(chlorobenzene or 1-chloro-4-methylbenzene) or the solvent wasremoved under reduced pressure. The residue obtained was puri-fied via silica gel chromatography (eluent: petroleum ether/ethylacetate = 10/1) to afford aryl iodides 2a–2o or heteroaryl iodides4a–4g.
Reference: [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1499 - 1503
[2] Synlett, 2013, vol. 24, # 20, p. 2730 - 2734
[3] Synthetic Communications, 2012, vol. 42, # 2, p. 170 - 175
[4] Journal of the American Chemical Society, 2015, vol. 137, # 26, p. 8328 - 8331
[5] Catalysis Today, 2016, vol. 274, p. 129 - 132
[6] Catalysis Science and Technology, 2017, vol. 7, # 10, p. 2110 - 2117
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  • [ 580-13-2 ]
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  • [ 13720-06-4 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 525,535
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  • [ 10035-10-6 ]
  • [ 7705-08-0 ]
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  • [ 13720-06-4 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 525,535
  • 12
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  • [ 16650-55-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 6, p. 2067 - 2081
  • 13
  • [ 90-11-9 ]
  • [ 607-58-9 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 16, p. 4340 - 4343
[2] Green Chemistry, 2015, vol. 17, # 7, p. 3910 - 3915
  • 14
  • [ 90-11-9 ]
  • [ 67-64-1 ]
  • [ 6301-54-8 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 1.5 h; Inert atmosphere
To a stirred solution of 1-bromonaphthalene (12, 41.41 g,0.2 mol) in dried THF (400 mL) held at -78 °C in N2 atmosphere was added dropwise 1.6 M n-BuLi in n-hexane (125mL, 0.2 mol) via syringe, and after addition the resulting solution was stirred at -78 °C for 1 h before dropwise addition of dried acetone (17.42 g, 0.3 mol) via syringe. Thereafter the reaction mixture was stirred for 0.5 h at -78 °C andfor another 1 h at room temperature. The reaction mixture was poured into ice-water (2 L) while stirring and the resulting mixture was stirred and extracted with CH2Cl2 (500 mL 3). The combined extracts were washed with 5percent brine(500 mL), dried (Na2SO4) and evaporated on a rotary evaporator to give a residue, which was purified by column chromatography followed by trituration with n-hexane/EtOAc(1/100 by v/v) to afford the pure product 2-(naphth-1-yl)-2-propanol (13) as colorless needles (33.90 g, 91percent). M.p. = 88.5-90 °C (literature value, 83-85 °C [18]). 1H NMR(DMSO-d6, 400 MHz) : 8.84-8.87 (m, 1H), 7.87-7.90 (m,1H), 7.78 (d, 1H, J = 8.0 Hz), 7.56 (dd, 1H, J = 0.8 Hz and7.6 Hz), 7.43-7.49 (m, 2H), 7.40 (t, 1H, J = 7.8 Hz), 5.24 (s,1H), 1.70 (s, 6H).
Reference: [1] Medicinal Chemistry, 2017, vol. 13, # 3, p. 260 - 281
[2] Journal of Organic Chemistry, 2014, vol. 79, # 17, p. 8348 - 8357
[3] Journal fuer Praktische Chemie (Leipzig), 1987, vol. 329, # 3, p. 439 - 446
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  • [ 10075-63-5 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 28, p. 5603 - 5609
[2] Tetrahedron, 2002, vol. 58, # 28, p. 5603 - 5609
  • 16
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  • [ 85-46-1 ]
Reference: [1] Heteroatom Chemistry, 2007, vol. 18, # 3, p. 239 - 248
  • 17
  • [ 90-11-9 ]
  • [ 23719-80-4 ]
  • [ 25033-19-6 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: at 0 - 20℃; for 16 h;
Stage #2: With water; ammonium chloride In ethyl acetate
[00354] Cyclopropylmagnesium bromide (15OmL, 0.5M in tetrahydrofuran) was slowly added to a solution of 1 -bromonaphthalene (1Og, 50mmol) and [l ,3-bis(diphenylphosphino)ρroρane] dichloro nickel (II) in tetrahydrofuran (1OmL) stirred at 0°C, and the reaction mixture stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and ethyl acetate and aqueous ammonium chloride were added- After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield l-cyclopropylnaphthalcne (6.4g, 76percent).
76% at 0 - 20℃; for 16 h; Cyclopropylmagnesium bromide (150 niL, 0.5 M in tetrahydrofuran) was slowly added to a solution of 1-bromo-naphthalene (10 g, 50 mmol) and [1,3- bis(diphenylphosphino)propane]dichloronickel(II) in tetrahydrofuran (10 niL) stirred at 0 0C. The reaction mixture was stirred at room temperature for 16 hours and the solvent was evaporated under reduced pressure. EtOAc and ammonium chloride in water were added. After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1 -cyclopropyl-naphthalene (6.4 g, 76percent).
76% at 0 - 20℃; STEP A: 1-CyclopropylnaphthaleneCyclopropylmagnesium bromide (150 mL, 0.5M in tetrahydrofuran) was slowly added to a solution of 1-bromonaphthalene (10 g, 50 mmol) and [l,3-bis(diphenylphosphino)propane] dichloro nickel (II) in tetrahydrofuran (10 mL) stirred at 0 °C, and the reaction mixture stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and ethyl acetate and aqueous ammonium chloride were added. After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1-cyclopropylnaphthalene (6.4 g, 76percent).
Reference: [1] Patent: WO2009/70740, 2009, A2, . Location in patent: Page/Page column 89
[2] Patent: WO2006/26356, 2006, A2, . Location in patent: Page/Page column 20
[3] Patent: WO2011/85009, 2011, A2, . Location in patent: Page/Page column 36
[4] Patent: WO2014/8295, 2014, A1, . Location in patent: Paragraph 0345-0348
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  • [ 411235-57-9 ]
  • [ 25033-19-6 ]
YieldReaction ConditionsOperation in experiment
57% With potassium phosphate tribasic heptahydrate; C45H53ClFeNO2PPd In water; toluene at 100℃; for 5 h; Inert atmosphere General procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol percent) was added to the solution of aryl halides (0.25 mmol) and cyclopropylboronic acid (0.5 mmol) in toluene (2.0 mL) and water (100 μL). The mixture was heated to 100 °C for a proper time under nitrogen atmosphere and cooled to room temperature. Water (10 mL) was added and the mixture was extracted with EtOAc (3.x.15 mL), evaporated and purified by chromatography on silica gel.
Reference: [1] Synthetic Communications, 2006, vol. 36, # 1, p. 121 - 128
[2] Tetrahedron, 2012, vol. 68, # 3, p. 900 - 905
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  • [ 50-00-0 ]
  • [ 90-11-9 ]
  • [ 79996-99-9 ]
Reference: [1] Journal of the Chemical Society, 1962, p. 3915 - 3926
  • 20
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  • [ 762-04-9 ]
  • [ 13440-07-8 ]
Reference: [1] Chemical Communications, 2010, vol. 46, # 30, p. 5443 - 5445
  • 21
  • [ 90-11-9 ]
  • [ 91-20-3 ]
  • [ 13440-07-8 ]
  • [ 3411-48-1 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: at 70℃; for 3 h;
To a solution of t-BuOK (8.14 g, 72.5 mmol) in anhydrous and degassed DMSO (73 mL), blown with argon and saturated with dry phosphine, a solution of 1-bromonaphthalene (10.01 g, 48.3 mmol) in anhydrous DMSO (7 mL) was added dropwise at 70 °C for 1 h under stirring and continuous bubbling of the phosphine. The reaction mixture was heated (70 °C) for 0.5 h in the flow of phosphine, the phosphine feeding was stopped, but the mixture was continuously stirred for 1.5 h (70 °C). In the 31P NMR spectrum of the reaction mixture, the following signals were observed: −62.03 (d, 1JPH 227 Hz) for 1-Np2PH, −33.37 (s) for 1-Np3P and −2.49 (t, 1JPH 463Hz) for 1-NpP(O)H2 in a ratio of ∼5:1.5:0.1. Trace amounts of 1,2-Np2PH (−49.78 ppm) and 1,1,2-Np3P (−22.70 ppm) were also formed. Then the mixture was blown with argon, cooled and diluted with cold water (80 mL) to give a white precipitate (1.15 g). The latter was filtered off, washed with water (5×30 mL) and Et2O (3×25 mL), dried on the air to get 1-Np3P (0.68 g). The filtrate was sequentially extracted with Et2O (50 mL) and CH2Cl2 (2×50 mL). (a) Ether extract was washed with cold water (3×20 mL), dried over K2CO3, the solvent was removed under reduced pressure to give a white wax-like crude product (5.51 g), which was heated under 1 Torr (100–150 °C, sand bath) to sublimate naphthalene (1.37 g) and to distill unreacted BrNp (0.95 g, conversion 91 percent). The residue was dissolved in EtOH (22 mL), white precipitate was filtered off, washed with EtOH (10×5 mL) and dried in vacuo to give a creamy solid (0.62 g, 1-Np3P). Secondary phosphine oxide 1-Np2P(O)H (2.30 g) was isolated from alcoholic extract after removing the solvent and drying in vacuum. b) CH2Cl2 extract was washed with brine (10 percent aq. sol. KCl), orange precipitate was filtered off, dried over K2CO3 and the solvent was removed to give white wax-like product (1.21 g). The latter was heated under 1 Torr (100–150 °C, sand bath) to sublimate naphthalene (0.17 g), the residue was washed with EtOH (3×20mL), the 1-Np3P (0.08 g) was filtered off, EtOH was removed to afford 1-Np2P(O)H (0.65 g). Total yield of 1-Np2P(O)H is 2.95 g (45 percent). Total yield of 1-Np3P is 1.38 g (23 percent). Yield of naphthalene is 1.54 g (27 percent).
Reference: [1] Tetrahedron, 2017, vol. 73, # 32, p. 4723 - 4729
  • 22
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  • [ 13440-07-8 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 49, p. 17595 - 17599
  • 23
  • [ 1069-08-5 ]
  • [ 90-11-9 ]
  • [ 13440-07-8 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 17, p. 6106 - 6109
  • 24
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  • [ 3411-48-1 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 3, p. 694 - 697
[2] Applied Catalysis A: General, 2012, vol. 419-420, p. 185 - 193
[3] Journal of Organic Chemistry, 1978, vol. 43, p. 2941 - 2946
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  • [ 91-20-3 ]
  • [ 13440-07-8 ]
  • [ 3411-48-1 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: at 70℃; for 3 h;
To a solution of t-BuOK (8.14 g, 72.5 mmol) in anhydrous and degassed DMSO (73 mL), blown with argon and saturated with dry phosphine, a solution of 1-bromonaphthalene (10.01 g, 48.3 mmol) in anhydrous DMSO (7 mL) was added dropwise at 70 °C for 1 h under stirring and continuous bubbling of the phosphine. The reaction mixture was heated (70 °C) for 0.5 h in the flow of phosphine, the phosphine feeding was stopped, but the mixture was continuously stirred for 1.5 h (70 °C). In the 31P NMR spectrum of the reaction mixture, the following signals were observed: −62.03 (d, 1JPH 227 Hz) for 1-Np2PH, −33.37 (s) for 1-Np3P and −2.49 (t, 1JPH 463Hz) for 1-NpP(O)H2 in a ratio of ∼5:1.5:0.1. Trace amounts of 1,2-Np2PH (−49.78 ppm) and 1,1,2-Np3P (−22.70 ppm) were also formed. Then the mixture was blown with argon, cooled and diluted with cold water (80 mL) to give a white precipitate (1.15 g). The latter was filtered off, washed with water (5×30 mL) and Et2O (3×25 mL), dried on the air to get 1-Np3P (0.68 g). The filtrate was sequentially extracted with Et2O (50 mL) and CH2Cl2 (2×50 mL). (a) Ether extract was washed with cold water (3×20 mL), dried over K2CO3, the solvent was removed under reduced pressure to give a white wax-like crude product (5.51 g), which was heated under 1 Torr (100–150 °C, sand bath) to sublimate naphthalene (1.37 g) and to distill unreacted BrNp (0.95 g, conversion 91 percent). The residue was dissolved in EtOH (22 mL), white precipitate was filtered off, washed with EtOH (10×5 mL) and dried in vacuo to give a creamy solid (0.62 g, 1-Np3P). Secondary phosphine oxide 1-Np2P(O)H (2.30 g) was isolated from alcoholic extract after removing the solvent and drying in vacuum. b) CH2Cl2 extract was washed with brine (10 percent aq. sol. KCl), orange precipitate was filtered off, dried over K2CO3 and the solvent was removed to give white wax-like product (1.21 g). The latter was heated under 1 Torr (100–150 °C, sand bath) to sublimate naphthalene (0.17 g), the residue was washed with EtOH (3×20mL), the 1-Np3P (0.08 g) was filtered off, EtOH was removed to afford 1-Np2P(O)H (0.65 g). Total yield of 1-Np2P(O)H is 2.95 g (45 percent). Total yield of 1-Np3P is 1.38 g (23 percent). Yield of naphthalene is 1.54 g (27 percent).
Reference: [1] Tetrahedron, 2017, vol. 73, # 32, p. 4723 - 4729
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  • [ 91-20-3 ]
  • [ 3411-48-1 ]
Reference: [1] Heteroatom Chemistry, 2011, vol. 22, # 2, p. 198 - 203
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  • [ 90-11-9 ]
  • [ 67-68-5 ]
  • [ 91-20-3 ]
  • [ 13183-58-9 ]
  • [ 3411-48-1 ]
  • [ 7402-93-9 ]
Reference: [1] Heteroatom Chemistry, 2011, vol. 22, # 2, p. 198 - 203
  • 28
  • [ 90-11-9 ]
  • [ 39864-75-0 ]
  • [ 3411-48-1 ]
Reference: [1] Tetrahedron, 2017, vol. 73, # 32, p. 4723 - 4729
  • 29
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  • [ 43038-45-5 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9550 - 9555
  • 30
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  • [ 204530-94-9 ]
Reference: [1] Patent: KR2017/49295, 2017, A,
  • 31
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  • [ 103986-53-4 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 33, p. 8609 - 8613
  • 32
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  • [ 63628-25-1 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 30, p. 4114 - 4116
  • 33
  • [ 90-11-9 ]
  • [ 5500-21-0 ]
  • [ 77972-87-3 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 32, p. 3351 - 3353
  • 34
  • [ 90-11-9 ]
  • [ 1079-66-9 ]
  • [ 153725-04-3 ]
Reference: [1] Synthetic Communications, 1995, vol. 25, # 11, p. 1741 - 1744
  • 35
  • [ 90-11-9 ]
  • [ 572-83-8 ]
  • [ 474688-76-1 ]
YieldReaction ConditionsOperation in experiment
64% With Ki In tetrahydrofuran; n-butyllithium; toluene 3-1)
Synthesis of 2-bromo-9,10-di(naphthyl)anthracene
360 g (1.74 mol) of bromonaphthalene was dissolved with THF in a 5 L flask and the temperature was lowered to -78° C. and 1600 ml (1.6 mol) of 1.6M n-BuLi was slowly added dropwise thereto.
The mixture was stirred for one hour, and then 200 g (0.68 mol) of 2-bromoanthraquinone was added thereto in a solid state and then the temperature was slowly raised to room temperature and the resultant mixture was stirred.
After 12 hours, 500 ml of 2N HCl(aq) was added thereto.
Then, an organic layer was isolated and dried over MgSO4 and condensed under reduced pressure, thereby producing Compound C.
The Compound C was used in the subsequent reaction without purification.
Compound C, 346 g (2.09 mol) of KI, and 443 g (4.1 mol) of NaH2PO2.H2O were diluted with an acetic acid and then the mixture was refluxed while heating.
The temperature was lowered to room temperature and thus a solid was precipitated.
The solid was filtered, washed with excess water and MeOH, and re-crystallized with 300 ml of toluene, thereby producing 2-bromo-9,10-di(2-naphthyl)anthracene (230 g, 64percent).
Reference: [1] Patent: US2011/31484, 2011, A1,
  • 36
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  • [ 878671-94-4 ]
Reference: [1] Patent: WO2011/85009, 2011, A2,
[2] Patent: WO2014/8295, 2014, A1,
  • 37
  • [ 90-11-9 ]
  • [ 878671-96-6 ]
Reference: [1] Patent: WO2011/85009, 2011, A2,
  • 38
  • [ 90-11-9 ]
  • [ 4612-28-6 ]
  • [ 881913-20-8 ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 2 h; 1,3PhenylDiboronAcid 1.99g (12mmol), 1- bromo-naphthalene 2.07g (10mmol), Pd (PPh3) 4 (0.58 g, 0.5mmol) and potassium carbonate (4.15g, 30mmol) and THF: H2O = 2: 1 solution to 100ml were dissolved was stirred for 2 hours under reflux at 80 . After this was added the organic layer was dried H2O40ml obtained by extraction three times with ethyl ether 40ml magnesium sulfate, and the solvent evaporatedObtained by purification of the residue by silica gel column chromatography to give the intermediate D-2 (1.74g, 70percent yield).
Reference: [1] Patent: KR2016/30001, 2016, A, . Location in patent: Paragraph 0368-0371
  • 39
  • [ 90-11-9 ]
  • [ 1151516-14-1 ]
Reference: [1] Patent: WO2011/85009, 2011, A2,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
[4] Patent: WO2014/8295, 2014, A1,
[5] Patent: WO2014/8295, 2014, A1,
[6] Patent: WO2014/8295, 2014, A1,
[7] Patent: WO2014/8295, 2014, A1,
  • 40
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  • [ 400607-04-7 ]
Reference: [1] Patent: KR2015/22269, 2015, A,
[2] Patent: KR2017/49295, 2017, A,
  • 41
  • [ 90-11-9 ]
  • [ 1533519-92-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
  • 42
  • [ 90-11-9 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
  • 43
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  • [ 1533519-85-5 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
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[ 90-11-9 ]

Chemical Structure| 37621-57-1

A1529308[ 37621-57-1 ]

1-Bromonaphthalene-2,3,4,5,6,7,8-d7

Reason: Stable Isotope