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Chemical Structure| 91-16-7
Chemical Structure| 91-16-7
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Product Details of [ 91-16-7 ]

CAS No. :91-16-7 MDL No. :MFCD00008357
Formula : C8H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ABDKAPXRBAPSQN-UHFFFAOYSA-N
M.W :138.16 Pubchem ID :7043
Synonyms :
1,2-Dimethoxybenzene

Calculated chemistry of [ 91-16-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.43
TPSA : 18.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : 1.7
Log Po/w (MLOGP) : 1.48
Log Po/w (SILICOS-IT) : 1.82
Consensus Log Po/w : 1.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.02
Solubility : 1.33 mg/ml ; 0.00962 mol/l
Class : Soluble
Log S (Ali) : -1.6
Solubility : 3.48 mg/ml ; 0.0252 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.62
Solubility : 0.329 mg/ml ; 0.00238 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 91-16-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 91-16-7 ]

* 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 [ 91-16-7 ]
  • Downstream synthetic route of [ 91-16-7 ]

[ 91-16-7 ] Synthesis Path-Upstream   1~67

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[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 934 - 946
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  • 11
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YieldReaction ConditionsOperation in experiment
97% With bromine In tetrachloromethane at 0 - 5℃; for 2.5 h; Preparation A
1,2-dibromo-4,5-dimethoxybenzene
16.16 g of 1,2-dimethoxybenzene (117 mmol) are stirred at 0° C. in CCl4 (120 mL).
13.2 mL of dibromine (2.2 eq; 257.4 mmol; 41.13 g) dissolved in CCl4 (25 mL) are added dropwise (30 min) whilst monitoring the temperature (0-5° C.) [Fit an outlet which bubbles into a solution of Na2CO3 in order to neutralise the hydrobromic acid which forms].
After stirring for 2 hours at 0° C., the reaction mixture is then poured onto a mixture of water+ice, and the organic phase is washed with aqueous 10percent NaHSO3 solution and then with aqueous 10percent NaOH solution.
After evaporation and drying, 33.42 g of a white solid corresponding to the title product are obtained.
Yield=97percent
m.p. 92-93° C.
1H NMR (CDCl3): δ=7.06 (s; 2H); 3.86 (s; 6H).
13C NMR (CDCl3): δ=148.8; 115.9; 114.7; 56.2.
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[2] Journal of the American Chemical Society, 1980, vol. 102, # 9, p. 3056 - 3062
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YieldReaction ConditionsOperation in experiment
91% With dihydrogen peroxide; ammonium bromide; acetic acid In water at 20℃; for 20 h; Example 1 : Preparation of 4-bromo-1.2-dimethoxybenzene (1) from veratrole A 3.0 L reactor was charged with veratrole (142 g, 1.03 mol) and ammonium bromide (110 g, 1.12 mol, 1.10 equiv) in acetic acid (1.6 L). Aqueous hydrogen peroxide (30percent) (180 mL, 1.76 mol, 1.67 equiv) was added dropwise to the reaction mixture and the contents allowed to stir at room temperature. After 20 h, the reaction mixture was treated with saturated sodium bicarbonate solution and extracted with dichloromethane (3 χ 200 mL). The combined organic extract was washed with water (2 χ 200 mL) and brine (200 mL), dried over anhydrous sodium sulfate, and then evaporated under reduced pressure to give a yellow liquid. After distillation, the pure product (202.7 g, b.p. 128-133 °C/10 mbar, 91percent) was obtained. 3/4 NMR (400 MHz, DMSO-13C NMR (100 MHz, DMSO-"3/4): δ 150.3, 148.8, 123.5, 115.3, 113.8, 112.3, 56.2, 56.0.
87% With N-Bromosuccinimide; silica gel; toluene-4-sulfonic acid In dichloromethane at 0 - 20℃; for 3 h; Inert atmosphere General procedure: To a solution of compounds 20b and 20c (75 mmol) in dichloromethane (210 mL) containing TsOH (10mmol), silica gel G 60 230-400 mesh (37 g) in nitrogen atmosphere at 0 °C, was added NBS (75 mmol) slowly.The reaction was stirred at room temperature by 3 hours.The work up was performed with 300 mL of saturated NaHCO3 solution and the product was extracted with ethylacetate (3 × 150 mL). The organic phase was dried over MgSO4 and the solvent removed under reduced pressure.The products were purified by distillation at low pressure (3 mmHg). 4-Bromo-1,2-dimethoxybenzene (21b) Yield: 87percent; colorless oil; 1H NMR (300 MHz, CDCl3)d 3.84 (s, 3H, OCH3), 3.85 (s, 3H, OCH3), 6.73 (d, 1H,J 8.3 Hz, Ph-H), 6.98 (d, 1H, J 1.6 Hz, Ph-H), 7.03 (dd, 1H,J 8.3, 1.6 Hz, Ph-H); 13C NMR (75 MHz, CDCl3) d 55.97,112.56, 112.66, 114.80, 123.34, 148.36, 149.78.
83 %Chromat. With carbon dioxide; oxygen; lithium bromide; copper(ll) bromide In water at 100℃; for 12 h; Autoclave; Green chemistry General procedure: A mixture of substrate (1 mmol), CuBr2 (22.4 mg, 10 molpercent), LiBr (130.3 mg, 1.5 equiv.), and 0.05 mL of water was placed in a 50 mL stainless steel autoclave equipped with an inner glass tube in room temperature. CO2 (4 MPa) and O2 (1 MPa) were subsequently introduced into the autoclave and the system was heated under the predetermined reaction temperature for 15 min to reach the equilibration. Then the final pressure was adjusted to the desired pressure by introducing the appropriate amount of CO2. The mixture was stirred continuously for the desired reaction time. After cooling, products were diluted with acetone and analyzed by gas chromatograph (Shimadzu GC-2014) equipped with a capillary column (RTX-17 30 m × 25 μm and RTX-wax 30 m × 25 μm) using a flame ionization detector by comparing the retention times of authentic samples. The residue was purified by column chromatography on silica gel (200–300 mesh, eluting with petroleum ether/ethyl acetate from petroleum ether to 50:1) to afford the desired product. The isolated products were further identified with NMR spectra (Bruker 400 MHz) and GC–MS or GCD, which are consistent with those reported in the literature.
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YieldReaction ConditionsOperation in experiment
90.1% at 25℃; for 24 h; A type B crystal of 2,3,6,7,10,11-hexahydroxytriphenylene monohydrate was synthesized according to the process described in Synthesis, 477, 1994 and JP-A-8-119894. Namely, 1,2-dimethoxybenzene (31.78 g, 0.23 moles) and anhydrous ferric chloride (120 g, 0.74 moles) were dissolved in 70percent sulfuric acid, and the solution was reacted at 25°C for 24 hours with stirring. After completion of the reaction, the solution was poured into ice water (500 g), and the precipitated crystal was collected by filtration. After the resultant crystal was washed with water (1 L), and then dried to give pale purple colored 2,3,6,7,10,11-hexamethoxytriphenylene (28.2 g, theoretical yield from 1,2-dimethoxybenzene: 90.1percent) (the method of Synthesis, 477, 1994).
85.4% at 10 - 15℃; for 6 h; 600 ml of ethyl acetate was added into a 1000ml four-necked flask, sodium peroxydisulfate 102.4g (0.43 mol) and o-xylene 45.7 g (0.43 mol) were added, stirred and cooled at internal temperature of 10 degrees C. Anhydrous iron(III) chloride 345.4g (2.10 mol) was added little by little, reacted at an internal temperature of 10-15 degrees C for 6 hours. After completion of the reaction, reaction mixture was cooled, 2000 ml of water was added and stirred for 10minutes. The aqueous layer of the solution was separated, and the organic layer was washed with 800 ml of salt solution. 600 ml of methanol was added to the organic layer and crystallized at 15-25 degrees C for 1 hour, the crystals were filtered, and dried to obtain 19.5 g (43.6percent of yield) of objects as gray crystal.
82% With trifluorormethanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 10 h; Inert atmosphere General procedure: An oven-dried 20 mL scintillation vial, equipped with a magnetic stir-bar, was charged with the starting material (1.0 equiv), DDQ (1.0 equiv), trifluoromethanesulfonic acid (1.4percent v/v, 3.0 equiv), and 1,2-dichloroethane (0.05 M). The reaction mixture was then allowed to stir at ambient temperature for 10 h. After this time, methanol (0.05M) was added, and the solution was then allowed to stir at ambient temperature for an additional hour. Upon addition of the methanol, some solids precipitated out of the solution. Then, the solvent was removed from the heterogeneous mixture under reduced pressure. The crude material was purified by either recrystallization (methanol/DCM) or silica-gel column chromatography (hexanes/DCM) to give the title compounds.
80% With iron(III) chloride; sulfuric acid In dichloromethane at 20℃; for 3 h; A solution of 1,2-dimethoxybenzene (10 g, 72.4 mmol) in dichloromethane(50 ml) was added dropwise to a suspension of anhydrous FeCl3 (35.22 g, 217.2 mmol) in dichloromethane (100 ml) and concentrated sulphuric acid (0.5 ml). After complete addition (15 min), the reaction mixture was further stirred for 3 h at room temperature. 200 ml of methanol were then slowly added under vigorous stirring. The obtained mixture was further stirred for additional 30 min. And the precipitate was filtered off, washed with methanol (5 × 100 ml) and dried under reduced pressure to give a purple solid. Yield: 80percent, 1HNMR (CDCl3) δ/ppm: 4.10 (s, 18H, OCH3), 7.80 (s, 6H, ArH).

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[24] Chimia, 2015, vol. 69, # 9, p. 520 - 523
[25] Patent: JP2017/31106, 2017, A, . Location in patent: Paragraph 0052-0055
[26] Journal of Materials Chemistry A, 2017, vol. 5, # 24, p. 12080 - 12085
  • 30
  • [ 91-16-7 ]
  • [ 1004-66-6 ]
  • [ 808-57-1 ]
  • [ 47075-39-8 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 5, p. 317 - 326
  • 31
  • [ 91-16-7 ]
  • [ 808-57-1 ]
  • [ 152634-10-1 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 4, p. 465 - 466
  • 32
  • [ 91-16-7 ]
  • [ 1004-66-6 ]
  • [ 808-57-1 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 5, p. 317 - 326
  • 33
  • [ 91-16-7 ]
  • [ 161691-13-0 ]
  • [ 808-57-1 ]
  • [ 152634-10-1 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 4, p. 465 - 466
  • 34
  • [ 91-16-7 ]
  • [ 1004-66-6 ]
  • [ 808-57-1 ]
  • [ 47075-39-8 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 5, p. 317 - 326
  • 35
  • [ 91-16-7 ]
  • [ 808-57-1 ]
  • [ 139021-90-2 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408
  • 36
  • [ 91-16-7 ]
  • [ 14098-44-3 ]
  • [ 808-57-1 ]
  • [ 139021-90-2 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408
  • 37
  • [ 91-16-7 ]
  • [ 14098-24-9 ]
  • [ 808-57-1 ]
  • [ 139021-91-3 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408
  • 38
  • [ 91-16-7 ]
  • [ 67950-78-1 ]
  • [ 808-57-1 ]
  • [ 139021-92-4 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408
  • 39
  • [ 274-09-9 ]
  • [ 91-16-7 ]
  • [ 808-57-1 ]
  • [ 134025-14-2 ]
  • [ 134025-19-7 ]
Reference: [1] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798
  • 40
  • [ 91-16-7 ]
  • [ 4218-87-5 ]
  • [ 808-57-1 ]
  • [ 134025-12-0 ]
  • [ 134025-17-5 ]
  • [ 134025-07-3 ]
Reference: [1] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798
  • 41
  • [ 493-09-4 ]
  • [ 91-16-7 ]
  • [ 808-57-1 ]
  • [ 134025-10-8 ]
  • [ 134025-15-3 ]
  • [ 134025-08-4 ]
Reference: [1] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798
[2] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798
  • 42
  • [ 91-16-7 ]
  • [ 79-04-9 ]
  • [ 99-40-1 ]
Reference: [1] Journal of the Chemical Society, 1914, vol. 105, p. 1051
  • 43
  • [ 7446-70-0 ]
  • [ 91-16-7 ]
  • [ 98-95-3 ]
  • [ 79-04-9 ]
  • [ 99-40-1 ]
Reference: [1] Journal of the Chemical Society, 1914, vol. 105, p. 1051
  • 44
  • [ 91-16-7 ]
  • [ 4101-32-0 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 2, p. 474 - 491
[2] Bulletin of the Chemical Society of Japan, 2016, vol. 89, # 1, p. 125 - 134
  • 45
  • [ 91-16-7 ]
  • [ 124-38-9 ]
  • [ 1521-38-6 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With sodium In toluene
The ortho-metallation reaction is carried out as in Example 1, using different substrates and CO2 as electrophile.
Reference: [1] Angewandte Chemie - International Edition, 2002, vol. 41, # 2, p. 340 - 343
[2] Patent: US6384273, 2002, B1, . Location in patent: Page column 9
  • 46
  • [ 91-16-7 ]
  • [ 1521-38-6 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 1963,1965
  • 47
  • [ 109-72-8 ]
  • [ 91-16-7 ]
  • [ 60-29-7 ]
  • [ 124-38-9 ]
  • [ 1521-38-6 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 1963,1965
  • 48
  • [ 91-16-7 ]
  • [ 35202-54-1 ]
Reference: [1] Patent: US8859763, 2014, B1,
  • 49
  • [ 91-16-7 ]
  • [ 51560-21-5 ]
Reference: [1] Patent: US4647446, 1987, A,
  • 50
  • [ 91-16-7 ]
  • [ 5424-43-1 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; Petroleum ether at 20℃; for 2.5 h; Inert atmosphere
Stage #2: With bromine In diethyl ether; hexane at -78℃; for 0.5 h; Inert atmosphere
To a stirred solution of TMEDA (5.43 mL, 36.19 mmol, 1.0 equiv) in dry Et2O (100 mL) at room temperature was added n-BuLi (22.6 mL, 36.19 mmol, 1.0 equiv, 1.6 M solution in hexane).
The mixture was stirred for 10 min after which 1,2-dimethoxybenzene (5.0 g, 36.19 mmol) was added.
The reaction mixture was stirred at room temperature for 2.5 h, then cooled to -78 °C and a solution of bromine (1.85 mL, 36.19 mmol, 1.0 equiv) in dry hexane (10 mL) was added.
The reaction was maintained at -78 °C for 30 min and then allowed to warm to room temperature.
It was then quenched with satd aq Na2SO3 (20 mL).
The solution was extracted with EtOAc (3 * 30 mL) and the combined organic layers were washed with water, brine, dried (Na2SO4), and concentrated.
The residue was purified by silica gel column chromatography using petroleum ether/EtOAc (9.5:0.5 to 9:1) as eluent to give 1-bromo-2,3-dimethoxybenzene (6.68 g, 85percent) as a colorless oil
77%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 20℃; for 2 h;
Stage #2: With 1,2-dibromo-1,1,2,2-tetrachloroethane In diethyl ether; hexane at -78 - 20℃; for 0.166667 h;
n-BuLi 1.6M in hexane (70 mL, 112 mmol) was added dropwise at 0 0C to a solution of veratrole (10 g, 72.3 mmol) and TMEDA (10.9 mL, 72.3 mmol) in anhydrous ether (50 <n="53"/>mL) under nitrogen and stirred at room temperature for 2 h. The reaction mixture was cooled to -78 0C and (CBrCl2)2 (31.2 g, 112 mmol) was added, after stirring for a further 10 min, the cooling bath was removed and the reaction vessel allowed to warm to room temperature. The reaction mixture was diluted with ether (50 mL), washed with water (50 mL), IN HCl (2 x 50 mL), brine (50 mL) and dried over Na2SO4. The solvent was removed under vacuum and the crude product was purified by silica gel flash chromatography using hexane/DCM as eluent (5/1) to afford l-bromo-2,3-dimethoxy-benzene as a colourless oil (12.1 g, 77percent yield). 1H-NMR (CDCl3): 3.81 (s, 3H), 3.83 (s, 3H), 6.85 (d, J= 8.3 Hz, IH), 6.61-6.93 (m, IH), 6.96 (d, J= 8.3 Hz, IH).13C-NMR (CDCl3): 60.3, 60.6, 109.6, 111.7, 117.4, 132.1, 149.4, 151.5.
Reference: [1] Tetrahedron Asymmetry, 2013, vol. 24, # 24, p. 1548 - 1555
[2] Patent: WO2009/27679, 2009, A1, . Location in patent: Page/Page column 51-52
[3] Journal of Organic Chemistry, 1982, vol. 47, # 12, p. 2393 - 2396
  • 51
  • [ 91-16-7 ]
  • [ 74866-17-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 13, p. 2887 - 2896
  • 52
  • [ 91-16-7 ]
  • [ 4877-80-9 ]
Reference: [1] Journal of Materials Chemistry A, 2017, vol. 5, # 24, p. 12080 - 12085
[2] Journal of the American Chemical Society, 2017, vol. 139, # 46, p. 16759 - 16767
  • 53
  • [ 67-56-1 ]
  • [ 91-16-7 ]
  • [ 68-12-2 ]
  • [ 2150-42-7 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at -78 - 20℃; for 2 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 54
  • [ 91-16-7 ]
  • [ 79-22-1 ]
  • [ 2150-42-7 ]
Reference: [1] Synlett, 2005, # 3, p. 417 - 420
  • 55
  • [ 91-16-7 ]
  • [ 34006-60-5 ]
  • [ 18066-68-7 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1950, p. 1075,1078
  • 56
  • [ 91-16-7 ]
  • [ 23095-31-0 ]
Reference: [1] Journal of the Chemical Society, 1917, vol. 111, p. 957
[2] Journal of Medicinal Chemistry, 1977, vol. 20, # 10, p. 1235 - 1239
[3] Journal of the Chemical Society [Section] C: Organic, 1969, p. 1341 - 1345
  • 57
  • [ 91-16-7 ]
  • [ 121-43-7 ]
  • [ 40972-86-9 ]
YieldReaction ConditionsOperation in experiment
37%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether at -78℃; for 3 h;
Stage #2: at -78℃; for 18 h;
Stage #3: With hydrogenchloride In diethyl ether; water at 0℃; for 3 h;
[EXAMPLE 9: SYNTHESIS OF 6- (2, 3-DIMETHOXYPHENYL) -2,2-DIMETHYL-4-] phenethylsulfanylmethyl-1, 2-dihydroquinoline B (OH) Z Me MeO OMe I ~ (i li Suzuki Orme ZIZI \\/fizz OYE 9 To a solution [OF N, N, NAPOS;, NAPOS;-TETRAMETHYLETHYLENEDIAMINE] (6.1 mL, 40.5 mmol) in diethylether (100 mL) at [0°C] was added dropwise [N-BULI] (26 mL, 42 mmol). After 30 minutes, the reaction mixture was cooled to-78°C and 1,2-dimethoxybenzene was added dropwise. The reaction was stirred for 3 hours at that temperature. After the addition of trimethyl boronate (9.7 mL, 87 mmol), the cold bath was removed and the reaction stirred for 18 hours. After cooling to [0°C,] 150 mL [OF 2 M] aqueous [HC1] solution was added and the mixture was stirred for 3 hours. The mixture was extracted with three 20 mL portions of EtOAc, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 2,3-dimethoxy phenyl boronic acid as white crystals [(1] g, 37percent yield). 6-Bromo-2,2, [4-TRIMETHYL-1,] 2-dihydroquinoline (256 mg, 1.02 mmol) (Example 8) and 2,3- dimethoxyphenyl boronic acid (370 mg, 2.03 mmol) were combined in DMSO (2 mL). 2 M [K3PO4] (1 mL) was added, followed by [PDCL2] (dppf) (50 mg). The contents were placed in a microwave reaction vessel assembly and irradiated at [120°C] for 15 minutes. The reaction was cooled to room temperature. Purification of the crude product by chromatography afforded 6- (2,3-dimethoxyphenyl)-2, 2, [4-TRIMETHYL-1,] 2-dihydroquinoline (190 mg, [61percent)] as a white solid. Bromination with NBS followed by the coupling reaction with 2-phenylethanethiol using the procedures described in Example 7 provided 45 mg of the title compound as an oil.
Reference: [1] Chemical Communications, 1999, # 22, p. 2259 - 2260
[2] Patent: WO2004/18429, 2004, A2, . Location in patent: Page 85
[3] Bulletin de la Societe Chimique de France, 1973, p. 767 - 769
  • 58
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  • [ 40972-86-9 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 16, p. 5960 - 5967
  • 59
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  • [ 122775-35-3 ]
Reference: [1] Helvetica Chimica Acta, 2012, vol. 95, # 12, p. 2604 - 2620
  • 60
  • [ 91-16-7 ]
  • [ 73183-34-3 ]
  • [ 365564-10-9 ]
YieldReaction ConditionsOperation in experiment
98% With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)diiridium(I) dichloride In n-heptane at 25 - 95℃; Bis(pinacolato)diborone (19.68 g, 77.5 mmol), chloro(1 ,5-cyclooctadiene)iridium (I) dimer (0.33 g, 0.492 mmol) and bipiridyl (0.237 g, 1 .5 mmol) were added to the mixture of veratrol (10.0 g, 72.4 mmol) and n-heptane (60 mL) at 25 °C. The reaction mixture was warmed to 90 °C to 95 °C and was stirred for 16 -18 h. The reaction mixture was cooled to temperature 25 - 30 °C and ethyl acetate (50 mL) was added and mixture was stirred for 5 - 10 min. 1 N HCI solution (60 mL) was added to the reaction mixture and was stirred for 15 - 20 min. The reaction mixture was cooled to 25 °C and the organic layer was separated and was washed with brine (100 mL). The organic layer was dried over anhydrous sodium sulphate and the solvent was evaporated to obtain the title compound. Yield: 20 g (98 percent); 1H NMR (300 MHz, CDCI3): δ 7.4 (dd, 1 H, 1 .2 & 8.1 Hz), 7.3 (d, 1 H, 1 .2 Hz), 6.9 (d, 1 H, 8.1 Hz), 3.94 (s, 3H), 3.92 (s, 3H), 1 .36 (s, 12H); MS (ES+): 264 (M+1 ).
76.2% With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)diiridium(I) dichloride In n-heptane at 95℃; for 24 h; Inert atmosphere 3,4-Dimethoxyphenylboronic acid pinacol ester (1k) (403 mg, 76.2percent) was prepared from1,2-dimethoxybenzene (10) and bis(pinacolato)diboron according to the reported method.S53,4-Dimethoxyphenyl 4-tolyl sulfide (3t) (56.1 mg, 86.6percent) was prepared from S-(4-tolyl)4-toluenethiosulfonate (2a) and 3,4-dimethoxyphenylboronic acid pinacol ester (1k)according to the typical procedure for copper-catalyzed thiolation of boronic acid pinacolesters with thiosulfonates. To a mixture of bis(pinacolato)diboron (124 mg, 0.486 mmol, 0.96 equiv), 2,2'-bipyridyl(1.7 mg, 11 μmol, 2.2 mol percent), and [IrCl(cod)]2 (2.3 mg, 3.4 μmol, 0.68 mol percent) was added asolution of 1,2-dimethoxybenzene (10) (69.9 mg, 0.506 mmol, 1.0 equiv) dissolved inheptane (2.5 mL) was stirred at 95 °C for 24 h. After cooling to room temperature, themixture was concentrated under reduced pressure and used for next reaction without furtherpurification.To a mixture of S-(4-tolyl) 4-toluenethiosulfonate (2a) (69.1 mg, 0.248 mmol, 1.0 equiv),copper sulfate (2.0 mg, 13 μmol, 5.0 mol percent), and cesium fluoride (80.6 mg, 0.530 mmol, 2.1equiv) was added a solution of TMEDA (1.9 mg, 0.16 μmol, 6.6 mol percent) and the all amountof the crude mixture including 3,4-dimethoxyphenylboronic acid pinacol ester (1k) dissolvedin MeOH (2.5 mL), and the mixture was stirred at 50 °C for 24 h. After cooling to roomtemperature, the mixture was filtered through a pad of Celite, and then the filtrate wasconcentrated under reduced pressure. To the residue was added EtOAc (20 mL) and themixture was washed with aqueous saturated solution of sodium bicarbonate (20 mL × 2) andbrine (20 mL), and then dried (Na2SO4). After filtration, the filtrate was concentrated underreduced pressure. The residue was purified by preparative TLC (n-hexane/EtOAc = 10/1) togive 3,4-dimethoxyphenyl 4-tolyl sulfide (3t) (39.7 mg, 61.4percent) as a pale yellow oil.
Reference: [1] Patent: WO2013/175415, 2013, A1, . Location in patent: Page/Page column 46
[2] Journal of the American Chemical Society, 2015, vol. 137, # 7, p. 2665 - 2673
[3] Journal of the American Chemical Society, 2014, vol. 136, # 18, p. 6566 - 6569
[4] Journal of the American Chemical Society, 2002, vol. 124, # 3, p. 390 - 391
[5] Journal of the American Chemical Society, 2015, vol. 137, # 15, p. 5193 - 5198
[6] Chemistry Letters, 2018, vol. 47, # 1, p. 85 - 88
[7] Organometallics, 2010, vol. 29, # 13, p. 3019 - 3026
[8] Organometallics, 2010, vol. 29, # 13, p. 3019 - 3026
[9] Journal of the American Chemical Society, 2002, vol. 124, # 3, p. 390 - 391
[10] Angewandte Chemie - International Edition, 2013, vol. 52, # 3, p. 933 - 937[11] Angew. Chem., 2012, vol. 125, # 3, p. 967 - 971,5
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  • [ 25015-63-8 ]
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Reference: [1] Organic letters, 2001, vol. 3, # 18, p. 2831 - 2833
[2] Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 12, p. 1980 - 1982
[3] Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 12, p. 1980 - 1982
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Reference: [1] Organic Letters, 2008, vol. 10, # 12, p. 2597 - 2600
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Reference: [1] Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 12, p. 1980 - 1982
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  • [ 1196109-24-6 ]
  • [ 365564-10-9 ]
Reference: [1] Chemical Communications, 2010, vol. 46, # 41, p. 7724 - 7726
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Reference: [1] Chemical Communications, 2010, vol. 46, # 41, p. 7724 - 7726
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Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 49, p. 15765 - 15774
[2] Tetrahedron Letters, 2001, vol. 42, # 50, p. 8861 - 8864
[3] Journal of Coordination Chemistry, 2012, vol. 65, # 9, p. 1621 - 1631
[4] Organometallics, 2012, vol. 31, # 9, p. 3636 - 3646
[5] Tetrahedron Letters, 2013, vol. 54, # 26, p. 3419 - 3423
[6] Chemical Communications, 2014, vol. 50, # 46, p. 6161 - 6163
[7] Asian Journal of Chemistry, 2015, vol. 27, # 2, p. 654 - 656
[8] Chemistry Letters, 2015, vol. 44, # 9, p. 1257 - 1259
[9] Chemical Communications, 2016, vol. 52, # 14, p. 3003 - 3006
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Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 8, p. 2675 - 2687
[2] Patent: US2012/316342, 2012, A1,
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