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Structure of 352-67-0 * Storage: {[proInfo.prStorage]}
* 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] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9645 - 9649[2] Angew. Chem., 2018, vol. 130, p. 9793 - 9797,5
2
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]
Reference：
[1] Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13784 - 13789[2] Angew. Chem., 2018, vol. 130, p. 13980 - 13985,6
3
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]
Reference：
[1] Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13795 - 13799[2] Angew. Chem., 2018, vol. 130, # 42, p. 13991 - 13995,5
4
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]
Reference：
[1] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9645 - 9649[2] Angew. Chem., 2018, vol. 130, p. 9793 - 9797,5
5
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]
Reference：
[1] Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13784 - 13789[2] Angew. Chem., 2018, vol. 130, p. 13980 - 13985,6
6
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]
Reference：
[1] Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13795 - 13799[2] Angew. Chem., 2018, vol. 130, # 42, p. 13991 - 13995,5
7
[ 338792-64-6 ]
[ 352-67-0 ]
Yield
Reaction Conditions
Operation in experiment
19 %Spectr.
With silver trifluoromethanesulfonate; Selectfluor; trifluoroacetic acid In dichloromethane; water at 55℃; for 1 h; Inert atmosphere; Glovebox
General procedure: A microwave vial (5 mL) was sealed under an inert atmosphere (Argon glovebox) with a stir bar, Selectfluor (177.1 mg, 0.5 mmol, 2 equiv), silver trifluoromethanesulfonate (12.8 mg, 0.05 mmol, 20 molpercent) and aryloxydifluoroacetic acids (0.25 mmol, 1.0 equiv). To this vial DCM (1.8 mL), trifluoroacetic acid (76.5 μL, 1.0 mmol, 4.0 equiv) and water (0.2 mL) were injected. This mixture was heated for an hour at 55 °C. The resulting mixture was cooled down to room temperature, diluted with dichloromethane (4 mL), washed with water (3×5 mL), brine (5 mL), dried over anhydrous MgSO4 and filtered. The dried extract was concentrated on a rotary evaporator. The resulting crude product was dissolved in a small quantity of dichloromethane and loaded on to a silica cartridge (10 g, Biotage), airdried and eluted with pentane. The pure fractions were combined and the solvent was evaporated to obtain the pure products.
Reference：
[1] Organic Letters, 2016, vol. 18, # 15, p. 3754 - 3757
[2] Organic Letters, 2016, vol. 18, # 18, p. 4570 - 4573
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 33, p. 9758 - 9762[4] Angew. Chem., 2016, vol. 128, # 33, p. 9910 - 9914,5
[5] Journal of Fluorine Chemistry, 2017, vol. 203, p. 130 - 135
8
[ 371-41-5 ]
[ 352-67-0 ]
Reference：
[1] Organic Letters, 2016, vol. 18, # 18, p. 4570 - 4573
[2] Journal of Fluorine Chemistry, 2017, vol. 203, p. 130 - 135
Stage #1: With tert.-butyl lithium In tetrahydrofuran; pentane at -70℃; for 0.25 h; dry ice bath Stage #2: at -70 - 20℃; for 0.5 h; Stage #3: With water; ammonium chloride In tetrahydrofuran; pentane at 20℃;
EXAMPLE 49 3-Trifluoromethoxy-10-methyl-9H-imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4]benzodiazepine; a) 2-Fluoro-5-trifluoromethoxy-benzaldehyde; A solution of 1-fluoro-4-trifluoromethoxy-benzene (21.0 g, 117 mmol) in THF (233 ml) was cooled to <-70° C. Tert.-butyllithium (86 ml of a 1.5 molar solution in pentane, 129 mmol) was added at such a rate that temperature was kept <-70° C. Stirring in the dry ice bath was continued for 15 min, then DMF (11.6 ml, 150 mmol) was added dropwise keeping temperature <-70° C. After 30 min the reaction mixture was allowed to reach rt, quenched with saturated NH4Cl solution and extracted with ether. The organic phase was washed with brine, concentrated and chromatographed (SiO2, heptane:ethyl acetate=100:0 to 80:2). The title compound (11.0 g, 53percent) was obtained as a light yellow oil. 1H-NMR (300 MHz, DMSO): δ=7.60 (t, J=9.2 Hz, 1H), 7.75-7.85 (m, 2H), 10.20 (s, 1H).
With sulfuric acid; nitric acid; at 0℃; for 1.16667h;
A. 1 -Fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-Fluoro-2-nitro-1 - trifluoromethoxy-benzeneTo a mixture of <strong>[352-67-0]1-fluoro-4-trifluoromethoxy-benzene</strong> (31.57 g, 0.18 mol) in cone. H2SO4 (100 ml_) at 0C is added cone. HNO3 (30 ml_) dropwise over a 10 min period. After the mixture is stirred at 0 C for 1 h, it was poured into ice. The mixture is extracted with EtOAc. The organic extract is washed with H2O (3x) and brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 38 g (96%) of the product as a mixture of 1 -fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-fluoro-2-nitro-1 - trifluoromethoxy-benzene (-30/70, based upon 19F NMR). 1H NMR (CDCI3): delta 8.00- 7.90 and 7.80-7.65 (m, 1 H), 7.60-7.25 (m, 2H); 19 F NMR (CDCI3) delta -57.59 and -58.11 (s, 3F), -109.07 and -117.90 (t, J = 6.2 and d, J = 6.2, 1 F).
...presented by the following formula (4) which can respectively correspond to the formula (1) can be obtained. (D) Fluorine substituted aromatic compound represented by the formula (4) corresponding to the hydroxy compound wherein X1 is a substituent of the group (a) in the formula(1): ... 2-trifluoromethylfluorobenzene, 3-trifluoromethylfluorobenzene, 4-trifluoromethylfluorobenzene, 2-trichloromethylfluorobenzene, 3-trichloromethylfluorobenzene, 4-trichloromethylfluorobenzene, 2-trifluoromethoxyfluorobenzene, 3-trifluoromethoxyfluorobenzene, 4-trifluoromethoxyfluorobenzene, 2-trichloromethoxyfluorobenzene, 3-trichloromethoxyfluorobenzene, 4-trichloromethoxyfluorobenzene, 2-fluorophenylmethylsulfone, 3-fluorophenylmethylsulfone, 4-fluorophenylmethylsulfone, 2-hydroxydiphenylsulfone, ...
At -10 C, 90% fuming nitric acid (25mL) was added to concentrate sulfuric acid (50 mL) slowly to keep the temperature below 0 C. At -20 C, <strong>[352-67-0]1-fluoro-4-trifluoromethoxy-benzene</strong> (5 g, 27.7 mmol) was added portionwise to keep the temperature of the reaction mixture below 0 C. After addition, the reaction mixture was kept at 0 C for 30 min, poured into ice-water, extracted with EtOAc. The extracts were concentrated to give a mixture (6.05 g) of 4-fluoro-2-nitro-1-trifluoromethoxy-benzene and 1-fluoro-2-nitro-4-trifluoromethoxy-benzene in a 3:1 ratio.
Boron trifluoride etherate (0.453 ml, 3.89 mmol) and trimethyl borate (0.867 ml, 7.77 mmol) were stirred in anhydrous tetrahydrofuran (THF, 10 ml) for 10 minutes to form dimethoxyfluoroborane in situ.To a solution of the <strong>[352-67-0]4-fluoro(trifluoromethoxy)benzene</strong> (2.0 g, 11.1 mmol) in dry THF (30 ml) at -780C, was added ethylenediaminetetraacetic acid (EDTA, 1.36 g, 11.7 mmol) followed by a 1.4 M solution of sec-butyllithium in cyclohexane (8.33 ml, 11.7 mmol) and the reaction stirred for 2 hours under nitrogen. To this reaction mixture at - 780C, was then added dropwise the preformed dimethoxyfluoroborane mixture. The reaction was stirred at -780C for 30 minutes, warmed to room temperature for 30 minutes, and then quenched with water (10 ml). The volume of the reaction mixture was reduced in vacuo, then the residue dissolved in diethyl ether (10 ml) and washed with an aqueous solution of 10% NaOH (50 ml). The aqueous layer was acidified and extracted with ethyl acetate (3 x 40 ml). The combined ethyl acetate extracts were dried over MgSO4 and concentrated in vacuo to afford the title compound as a single regioisomer (1.51 g).LCMS Rt = 1.38 minMS m/z 223 [M]-
trans-4-(4-(trifluoromethoxy)phenoxy)cyclohexanamine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
To a stirred solution [OF TRANS-4-AMINOCYCLOHEXANOL (230] mg, [2MMOL)] in DMF (10 mL) at 0 C was added 60% NaH in mineral oil (240 mg, 6 mmol). The reaction mixture was stirred at 0 [C] [FOR'/2 HOUR] and then [1-FLUORO-4- (TRIFLUOROMETHOXY)] benzene (432 mg, 2.4 mmol) was added. It was heated to 60 [C] for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) [M/Z] 276 (M+H) [+.]
EXAMPLE 49 3-Trifluoromethoxy-10-methyl-9H-imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4]benzodiazepine; a) 2-Fluoro-5-trifluoromethoxy-benzaldehyde; A solution of 1-fluoro-4-trifluoromethoxy-benzene (21.0 g, 117 mmol) in THF (233 ml) was cooled to <-70 C. Tert.-butyllithium (86 ml of a 1.5 molar solution in pentane, 129 mmol) was added at such a rate that temperature was kept <-70 C. Stirring in the dry ice bath was continued for 15 min, then DMF (11.6 ml, 150 mmol) was added dropwise keeping temperature <-70 C. After 30 min the reaction mixture was allowed to reach rt, quenched with saturated NH4Cl solution and extracted with ether. The organic phase was washed with brine, concentrated and chromatographed (SiO2, heptane:ethyl acetate=100:0 to 80:2). The title compound (11.0 g, 53%) was obtained as a light yellow oil. 1H-NMR (300 MHz, DMSO): delta=7.60 (t, J=9.2 Hz, 1H), 7.75-7.85 (m, 2H), 10.20 (s, 1H).
A. 1 -Fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-Fluoro-2-nitro-1 - trifluoromethoxy-benzeneTo a mixture of <strong>[352-67-0]1-fluoro-4-trifluoromethoxy-benzene</strong> (31.57 g, 0.18 mol) in cone. H2SO4 (100 ml_) at 0C is added cone. HNO3 (30 ml_) dropwise over a 10 min period. After the mixture is stirred at 0 C for 1 h, it was poured into ice. The mixture is extracted with EtOAc. The organic extract is washed with H2O (3x) and brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 38 g (96%) of the product as a mixture of 1 -fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-fluoro-2-nitro-1 - trifluoromethoxy-benzene (-30/70, based upon 19F NMR). 1H NMR (CDCI3): delta 8.00- 7.90 and 7.80-7.65 (m, 1 H), 7.60-7.25 (m, 2H); 19 F NMR (CDCI3) delta -57.59 and -58.11 (s, 3F), -109.07 and -117.90 (t, J = 6.2 and d, J = 6.2, 1 F).B. 2-Fluoro-5-trifluoromethoxy-phenylamine and 5-Fluoro-2-trifluoromethoxy- phenvlamine A mixture of 1 -fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-fluoro-2-nitro-1 - trifluoromethoxy-benzene and Raney Ni (2800) in MeOH (250 ml_) is hydrogenated at 40 psi for 5 h (or until no more H2 is consumed). The catalyst is filtered off, and the filtrate is concentrated in vacuo. The residue is redissolved in CH2CI2, dried over MgSO4, filtered, and concentrated in vacuo to yield 27.4 g of the product (dark brown liquid) as a mixture of 2-fluoro-5-trifluoromethoxy-phenylamine and 5-fluoro-2- trifluoromethoxy-phenylamine (-30/70, based upon 19F NMR). 1H NMR (CDCI3): delta 7.15-6.90 (m, 1 H), 6.70-6.30 (m, 2H), 3.60-4.25 (br m, 1 H); 19 F NMR (CDCI3) delta -57.77 and -57.86 (s, 3F), -113.83 and -137.09 (1 H); MS 196 (M+1 , 100%).C. (delta-Fluoro^-trifluoromethoxy-phenvD-carbamic acid ethyl esterTo a solution of 2-fluoro-5-trifluoromethoxy-phenylamine and 5-fluoro-2- thfluoromethoxy-phenylamine (27.4 g, 0.14 mol) and pyridine (15.3 ml_) in THF (200 ml_) is added ethyl chloroformate (16.1 ml_, 0.19 mol) dropwise over a 3 min period. More pyridine and chloroformate (-1.8 eq) are added until all starting material disappears. The reaction mixture is partitioned between H2O and EtOAc. The two layers are separated, and the organic layer is washed with HCI (1 M), H2O, and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 70/30) as eluant to yield 22.66 g (60%) of the product as a yellow liquid. 1H NMR (CDCI3): delta 8.10-7.95 (m, 1 H), 7.25-7.15 (m, 1 H), 6.93 (br s, 1 H), 6.80-6.65 (m, 1 H), 4.27 (q, J = 7.2 Hz, 2H), 1.34 (t, J = 7.1 Hz, 3H); 19 F NMR (CDCI3) delta -58.53 (s, 3F), -112.08 (s, 1 F); MS 309 (M+CH3CN+1 , 100%), 268 (M+1 ).
A. 1 -Fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-Fluoro-2-nitro-1 - trifluoromethoxy-benzeneTo a mixture of <strong>[352-67-0]1-fluoro-4-trifluoromethoxy-benzene</strong> (31.57 g, 0.18 mol) in cone. H2SO4 (100 ml_) at 0C is added cone. HNO3 (30 ml_) dropwise over a 10 min period. After the mixture is stirred at 0 C for 1 h, it was poured into ice. The mixture is extracted with EtOAc. The organic extract is washed with H2O (3x) and brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 38 g (96%) of the product as a mixture of 1 -fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-fluoro-2-nitro-1 - trifluoromethoxy-benzene (-30/70, based upon 19F NMR). 1H NMR (CDCI3): delta 8.00- 7.90 and 7.80-7.65 (m, 1 H), 7.60-7.25 (m, 2H); 19 F NMR (CDCI3) delta -57.59 and -58.11 (s, 3F), -109.07 and -117.90 (t, J = 6.2 and d, J = 6.2, 1 F).B. 2-Fluoro-5-trifluoromethoxy-phenylamine and 5-Fluoro-2-trifluoromethoxy- phenvlamine A mixture of 1 -fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-fluoro-2-nitro-1 - trifluoromethoxy-benzene and Raney Ni (2800) in MeOH (250 ml_) is hydrogenated at 40 psi for 5 h (or until no more H2 is consumed). The catalyst is filtered off, and the filtrate is concentrated in vacuo. The residue is redissolved in CH2CI2, dried over MgSO4, filtered, and concentrated in vacuo to yield 27.4 g of the product (dark brown liquid) as a mixture of 2-fluoro-5-trifluoromethoxy-phenylamine and 5-fluoro-2- trifluoromethoxy-phenylamine (-30/70, based upon 19F NMR). 1H NMR (CDCI3): delta 7.15-6.90 (m, 1 H), 6.70-6.30 (m, 2H), 3.60-4.25 (br m, 1 H); 19 F NMR (CDCI3) delta -57.77 and -57.86 (s, 3F), -113.83 and -137.09 (1 H); MS 196 (M+1 , 100%).
7-bromo-3-[4-(trifluoromethoxy)phenyl]benzo[e]benzimidazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 160℃; for 16h;
Step 5: 7-bromo-3-[4-(trifluoromethoxy)phenyl]benzo[e]benzimidazole A stirred solution of the product of step 4 (15 g, 0.06 mol) and 1 -fluoro-4- (trifluoromethoxy)benzene (21 g, 0.12 mol) and Cs2C03 (50 g, 0.15 mol) in DMF (250 mL) was heated to 160C for 16h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried (MgS04) and concentrated to give 7- bromo-3-[4-(trifluoromethoxy)phenyl]benzo[e]benzimidazole 16 g (65% yield) which was used without further purification. LC/MS (method 1 ): Rt = 1.304 min; MS: m / z = 406.7 (M+).
With silver trifluoromethanesulfonate; Selectfluor; trifluoroacetic acid; In dichloromethane; water; at 55℃; for 1h;Inert atmosphere; Glovebox;
General procedure: A microwave vial (5 mL) was sealed under an inert atmosphere (Argon glovebox) with a stir bar, Selectfluor (177.1 mg, 0.5 mmol, 2 equiv), silver trifluoromethanesulfonate (12.8 mg, 0.05 mmol, 20 mol%) and aryloxydifluoroacetic acids (0.25 mmol, 1.0 equiv). To this vial DCM (1.8 mL), trifluoroacetic acid (76.5 muL, 1.0 mmol, 4.0 equiv) and water (0.2 mL) were injected. This mixture was heated for an hour at 55 C. The resulting mixture was cooled down to room temperature, diluted with dichloromethane (4 mL), washed with water (3×5 mL), brine (5 mL), dried over anhydrous MgSO4 and filtered. The dried extract was concentrated on a rotary evaporator. The resulting crude product was dissolved in a small quantity of dichloromethane and loaded on to a silica cartridge (10 g, Biotage), airdried and eluted with pentane. The pure fractions were combined and the solvent was evaporated to obtain the pure products.
2-(3,5-bis(trifluoromethyl)phenyl)-4-nitro-1-(trifluoromethoxy)-6-(trifluoromethyl)-1H-benzo[d]imidazole[ No CAS ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]
Yield
Reaction Conditions
Operation in experiment
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; In acetonitrile; at 20℃; for 16h;Glovebox; Irradiation; Sealed tube; Inert atmosphere;
General procedure: In a glovebox, to an oven-dried 20 mL screw cap vial was added 2- (3, 5-bis (trifluoromethyl) phenyl) -4-nitro-l- (trifluoromethoxy) -6- (trifluoromethyl) -lii-benzo [d] imidazole (1) (105 mg, 0.200 mmol, 1.00 equiv) , arene (2.00 mmol, 10.0 equiv) and Ru (bpy) 3 ( REe) 2, (0.0516 mg, 0.0600 pmol, 0.0300 moll) . Then MeCN (1.00 mL, 0.200 M) and a magnetic stir bar were added. The vial was capped and taken out of the glovebox. The reaction mixture was then stirred and irradiated with a 10 W LED (402 nm) at room temperature. After 16 h, an internal standard PhCF3 (5.84 mg, 4.95 pL, 0.04 mmol, 0.200 equiv) was added to the reaction vial, 0.200 mL of the resulting mixture was transferred to a 2 mL vial containing 0.500 mL of CDCI3. After the yield was determined using 19F NMR, the NMR sample was combined with the rest of the reaction mixture and the solvent was removed in vacuo. The crude material was purified by HPLC under noted conditions. The fractions containing the desired product were combined and extracted with CDCI3 (3 1 mL) , dried with magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to furnish the desired product of trifluoromethoxylation . For volatile compounds, after purification by HPLC, the desired product was extracted with 1 mL CDC13 and then directly characterized. The NMR peaks are referring to CH3CN residue signal ^H-NMR: d 1.94, 13C~NMR: 5 118.26, 1.32).2
3-methyl-4-nitro-1-(trifluoromethoxy)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-3-ium trifluoromethanesulfonate[ No CAS ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]
Yield
Reaction Conditions
Operation in experiment
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; In acetonitrile; at 20℃; for 16h;Glovebox; Irradiation; Sealed tube; Inert atmosphere;
General procedure: In a glovebox, to an oven-dried 20 mL screw cap vial was added 3- methyl-4-nitro-l- ( trifluoromethoxy) -6- (trifluoromethyl ) -1H- benzo[d] [1, 2, 3] triazol-3-ium trifluoromethanesulfonate (lb) (98.0 mg, 0.200 mmol, 1.00 equiv), arene (2.00 mmol, 10.0 equiv) and Ru (bpy) 3 (PFe) 2, (1.72 mg, 2.00 pmol, 1.00 mol%). Then MeCN (1.00 mL, 0.200 M) and a magnetic stir bar were added. The vial was capped and taken out of the glovebox. The reaction mixture was then stirred and irradiated with 2 of 10 W LED (Xmax = 447 nm) at room temperature. After 16 h, an internal standard PhCF3 (24.6 pL, 0.200 mmol, 1.00 equiv) was added to the reaction vial, 0.200 mL of the resulting mixture was transferred to a 2 mL vial containing 0.500 mL of CDC13. After the yield was determined using 19F NMR, the NMR sample was combined with the rest of the reaction mixture and the solvent was removed in vacuo. The crude material was purified by HPLC under noted conditions. The fractions containing the desired product were combined and extracted with CDC13 (3 x 10.0 mL) , dried with magnesium sulfate, and filtered unless otherwise noted. The filtrate was concentrated in vacuo to furnish the desired product of trifluoromethoxylation . For volatile compounds, after purification by HPLC, the desired product was extracted with 1 mL CDCI3 and then directly characterized. The NMR peaks are referring to CCN residue signal (1H-NMR : d 1.94, 13C-NMR: d 118.26, 1.32).2
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