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CAS No. : | 5400-80-6 | MDL No. : | MFCD00003798 |
Formula : | C9H9BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RTESDSDXFLYAKZ-UHFFFAOYSA-N |
M.W : | 213.07 | Pubchem ID : | 95444 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.1 |
TPSA : | 20.23 Ų |
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) : | -6.23 cm/s |
Log Po/w (iLOGP) : | 1.82 |
Log Po/w (XLOGP3) : | 1.93 |
Log Po/w (WLOGP) : | 1.72 |
Log Po/w (MLOGP) : | 2.25 |
Log Po/w (SILICOS-IT) : | 2.44 |
Consensus Log Po/w : | 2.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.78 |
Solubility : | 0.353 mg/ml ; 0.00166 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.98 |
Solubility : | 2.24 mg/ml ; 0.0105 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.05 |
Solubility : | 0.19 mg/ml ; 0.000891 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.58 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With H-β-zeolite In chlorobenzene at 120℃; for 6 h; | General procedure: In a 25 mL round bottomed flask, 250 mg (1.2 mmol) of 2-bromo-1-phenylethanol (1a), 50 mg (20 W/W percent) H-β-Zeolite and 1.0 mL of chlorobenzene were placed. The reaction flask was placed in an oil bath at 120°C for 6 h; the progress of the reaction was monitored by TLC. After completion of the reaction, the flask was allowed to attain room temperature, and filtered through Watt-Mann filter paper and washed with 10 mL of diethyl ether. Removal of the solvent under reduced pressure, the left out residue was purified by column chromatography on silica gel (200-400 mesh) and hexane as eluent to obtain 2a in (0.16 g) 72percent yield. |
70% | With toluene-4-sulfonic acid In toluene at 90℃; for 20 h; | (2) Synthesis of 2-bromoindene 25 g was taken from the bromohydrin compound obtained from the above reaction, dissolved in 300 mL of toluene, then 500 mg of p-toluene sulfonic acid was added thereto, and the temperature was raised to 90° C., and stirring was carried out for 20 h. After the reactant was cooled to room temperature, it was washed with a sufficient amount of water, dehydrated with MgSO4, and filtered and dried under reduced pressure, thereby obtaining a brown concentrate. This was dissolved in about 100 mL of hexane, and hexane was filtered as an eluent through a silica pad, thereby obtaining non-viscous yellow oil (2-bromoindene) in a yield of 60 to 70percent. 1H NMR (500 MHz, CDCl3): δ 3.61 (3H, s), 6.95 (1H, s), 7.18-7.20 (3H, m), 7.27-7.32 (1H, m), 7.39 (1H, m) |
60% | for 24 h; Heating | Indene (259 mmol, 30 g) and distilled water (9 mL) were put into dimethyl sulfoxide (DMSO, 90 mL), the temperature was decreased to 0°C, and N-bromosuccinimide (NBS, 263 mmol, 46.9 g) was slowly added thereto. The temperature of this solution was increased to normal temperature, and the solution was agitated for 12 hours. After that, after the reaction was finished by distilled water, the organic layer was extracted with diethyl ether, and moisture was removed by anhydrous magnesium sulfate. After the filtration under reduced pressure, compound B (38.9 g, 72percent) was obtained by removing the solvent by reducing the pressure of the filtered solution and recrystallizing the solution by hexane. 14.3 g of compound B and p-toluenesulfonic acid (p-TsOH, 2.6 mmol, 0.5 g) were dissolved in 60 mL of toluene, and agitated and heated for 24 hours while water was removed by using the Tin-Stock method. Compound C (7.8 g, 60percent) was obtained by decreasing the temperature of the solution to normal temperature and using the fractionation method. |
88.7 % | With p-toluenesulfonic acid monohydrate In chloroform; toluene | Preparation of 2-Bromoindene To a 500 mL flask containing a magnetic stir bar was added (+/-)trans-2-bromo-1-indanol (50.0 g, 235 mmol), p-toluenesulfonic acid monohydrate (0.50 g, 2.6 mmol), and toluene (300 mL). A Dean Stark trap and reflux condenser were placed on the flask, and the reaction was refluxed for 16 hours. The reaction was transferred to a separatory funnel, chloroform was added (200 mL), and the resulting mixture was washed with aqueous sodium bicarbonate solution (3*200 mL). The organic layer was then washed with a saturated aqueous sodium chloride solution (1*300 mL), dried over anhydrous magnesium sulfate, and filtered. The solvents were removed and distillation provided 40.6 g (88.7 percent) of the slightly yellow crystalline solid collected at 72-105° C. at 3 mm Hg. 1 H NMR (300 MHz, CDCl3, TMS); δ7.4-7.1(m, 4H), 6.93(s, 1H), 3.60(s, 2H). 13 C NMR (75 MHz, CDCl3): δ143.62, 142.22, 132.64, 126.38, 124.59, 124.49, 122.85, 119.88, 45.40. GC-MS: Calculated for C9 H7 79 Br 193.97, found 194.00. Calculated for C9 H7 81 Br 195.90, found 195.90. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With sodium hydroxide In diethyl ether at 20℃; for 12h; | |
With potassium hydroxide; diethyl ether | ||
With sodium hydrogencarbonate In methanol Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate at 140℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide nachfolgend Kochen mit Schwefelsaeure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tert.-butylhydroperoxide In dichloromethane for 6.5h; Ambient temperature; | |
With chromium(III) oxide; sulfuric acid at 50 - 70℃; | ||
With potassium dichromate; sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzene auf dem Waserbad; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzene at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80 - 90℃; anschliessend Behandeln mit Wasserdampf; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With N-Bromosuccinimide; water In dimethyl sulfoxide at 0℃; for 2.1h; | 1.1; 2.1 Example 1(1) Synthesis of Bromohydrin (1) Synthesis of Bromohydrin To a 500 mL flask, 35 mL (300 mmol) of indene was added, and diluted in 150 mL of DMSO and 15 mL of water. This solution was cooled to 0° C., and then 53 g of N-bromosuccinimide (300 mmol, 1 equiv.) was slowly added to the solution over 10 min. After 2 h, the reactant was poured into 800 mL of water, and the resulting crystal was washed with a sufficient amount of water while being filtered, thereby obtaining bromohydrin in the form of a while crystal in a yield of about 80%. 1H NMR (500 MHz, CDCl3): δ 3.24 (1H, m), 3.60 (1H, m), 4.30 (1H, m), 5.33 (1H, m), 7.23-7.32 (3H, m), 7.44 (1H, m) |
78% | With N-Bromosuccinimide; water In dimethyl sulfoxide for 15h; | |
72% | With N-Bromosuccinimide; water In dimethyl sulfoxide at 0 - 20℃; for 12h; | 4 Indene (259 mmol, 30 g) and distilled water (9 mL) were put into dimethyl sulfoxide (DMSO, 90 mL), the temperature was decreased to 0°C, and N-bromosuccinimide (NBS, 263 mmol, 46.9 g) was slowly added thereto. The temperature of this solution was increased to normal temperature, and the solution was agitated for 12 hours. After that, after the reaction was finished by distilled water, the organic layer was extracted with diethyl ether, and moisture was removed by anhydrous magnesium sulfate. After the filtration under reduced pressure, compound B (38.9 g, 72%) was obtained by removing the solvent by reducing the pressure of the filtered solution and recrystallizing the solution by hexane. 14.3 g of compound B and p-toluenesulfonic acid (p-TsOH, 2.6 mmol, 0.5 g) were dissolved in 60 mL of toluene, and agitated and heated for 24 hours while water was removed by using the Tin-Stock method. Compound C (7.8 g, 60%) was obtained by decreasing the temperature of the solution to normal temperature and using the fractionation method. |
With bromine; potassium bromide | ||
With bromine; potassium bromide | ||
With bromine; potassium bromide | ||
With bromine | ||
With water; bromine | ||
With N-Bromosuccinimide; water In acetone at 0℃; for 2h; | ||
733 mg | With N-Bromosuccinimide; water In tetrahydrofuran at 0 - 20℃; for 20h; | |
With N-Bromosuccinimide In water; dimethyl sulfoxide for 12h; | ||
Stage #1: 1-indene With N-Bromosuccinimide In water; dimethyl sulfoxide at 20℃; for 10h; Inert atmosphere; Schlenk technique; Stage #2: With water In dimethyl sulfoxide at 0℃; Inert atmosphere; Schlenk technique; | 3.10.3 Synthesis of 2-bromoindene To a mixture of indene (200mmol), distilled water (15ml) and dimethyl sulfoxide (70ml) was added portion wise an amount of 210mmol of N-bromosuccinimide. The resulting orange solution was stirred for 10h at room temperature, hydrolyzed with chilled water (100ml), and extracted with diethyl ether (3×100ml). The combined extracts were dried with magnesium sulphate and concentrated to give crystals of 2-bromoindan-1-ol upon standing overnight at -24°C. The obtained 2-bromoindan-1-ol (120mmol) was suspended in 100ml of toluene and mixed with a catalytic amount of para-toluenesulfonic acid monohydrate. The mixture was heated at reflux for 12h, and water was removed by a Dean-Stark apparatus. The resulting dark brown suspension was filtered and the volatiles were removed under vacuum. The residue was passed through silica gel using pentane as eluent, then the solvent was evaporated, and the crude product was distilled in vacuo. 2-Bromoindene was finally obtained as yellow crystals in 55% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With H-β-zeolite; In chlorobenzene; at 120℃; for 6h; | General procedure: In a 25 mL round bottomed flask, 250 mg (1.2 mmol) of 2-bromo-1-phenylethanol (1a), 50 mg (20 W/W %) H-β-Zeolite and 1.0 mL of chlorobenzene were placed. The reaction flask was placed in an oil bath at 120C for 6 h; the progress of the reaction was monitored by TLC. After completion of the reaction, the flask was allowed to attain room temperature, and filtered through Watt-Mann filter paper and washed with 10 mL of diethyl ether. Removal of the solvent under reduced pressure, the left out residue was purified by column chromatography on silica gel (200-400 mesh) and hexane as eluent to obtain 2a in (0.16 g) 72% yield. |
70% | With toluene-4-sulfonic acid; In toluene; at 90℃; for 20h; | (2) Synthesis of 2-bromoindene 25 g was taken from the bromohydrin compound obtained from the above reaction, dissolved in 300 mL of toluene, then 500 mg of p-toluene sulfonic acid was added thereto, and the temperature was raised to 90 C., and stirring was carried out for 20 h. After the reactant was cooled to room temperature, it was washed with a sufficient amount of water, dehydrated with MgSO4, and filtered and dried under reduced pressure, thereby obtaining a brown concentrate. This was dissolved in about 100 mL of hexane, and hexane was filtered as an eluent through a silica pad, thereby obtaining non-viscous yellow oil (2-bromoindene) in a yield of 60 to 70%. 1H NMR (500 MHz, CDCl3): δ 3.61 (3H, s), 6.95 (1H, s), 7.18-7.20 (3H, m), 7.27-7.32 (1H, m), 7.39 (1H, m) |
60% | toluene-4-sulfonic acid; In toluene; for 24h;Heating; | Indene (259 mmol, 30 g) and distilled water (9 mL) were put into dimethyl sulfoxide (DMSO, 90 mL), the temperature was decreased to 0C, and N-bromosuccinimide (NBS, 263 mmol, 46.9 g) was slowly added thereto. The temperature of this solution was increased to normal temperature, and the solution was agitated for 12 hours. After that, after the reaction was finished by distilled water, the organic layer was extracted with diethyl ether, and moisture was removed by anhydrous magnesium sulfate. After the filtration under reduced pressure, compound B (38.9 g, 72%) was obtained by removing the solvent by reducing the pressure of the filtered solution and recrystallizing the solution by hexane. 14.3 g of compound B and p-toluenesulfonic acid (p-TsOH, 2.6 mmol, 0.5 g) were dissolved in 60 mL of toluene, and agitated and heated for 24 hours while water was removed by using the Tin-Stock method. Compound C (7.8 g, 60%) was obtained by decreasing the temperature of the solution to normal temperature and using the fractionation method. |
40.6 g (88.7%) | With p-toluenesulfonic acid monohydrate; In chloroform; toluene; | Preparation of 2-Bromoindene To a 500 mL flask containing a magnetic stir bar was added (+/-)trans-2-bromo-1-indanol (50.0 g, 235 mmol), p-toluenesulfonic acid monohydrate (0.50 g, 2.6 mmol), and toluene (300 mL). A Dean Stark trap and reflux condenser were placed on the flask, and the reaction was refluxed for 16 hours. The reaction was transferred to a separatory funnel, chloroform was added (200 mL), and the resulting mixture was washed with aqueous sodium bicarbonate solution (3*200 mL). The organic layer was then washed with a saturated aqueous sodium chloride solution (1*300 mL), dried over anhydrous magnesium sulfate, and filtered. The solvents were removed and distillation provided 40.6 g (88.7 percent) of the slightly yellow crystalline solid collected at 72-105 C. at 3 mm Hg. 1 H NMR (300 MHz, CDCl3, TMS); δ7.4-7.1(m, 4H), 6.93(s, 1H), 3.60(s, 2H). 13 C NMR (75 MHz, CDCl3): δ143.62, 142.22, 132.64, 126.38, 124.59, 124.49, 122.85, 119.88, 45.40. GC-MS: Calculated for C9 H7 79 Br 193.97, found 194.00. Calculated for C9 H7 81 Br 195.90, found 195.90. |
With toluene-4-sulfonic acid; In toluene; for 12h;Inert atmosphere; Schlenk technique; Reflux; | To a mixture of indene (200mmol), distilled water (15ml) and dimethyl sulfoxide (70ml) was added portion wise an amount of 210mmol of N-bromosuccinimide. The resulting orange solution was stirred for 10h at room temperature, hydrolyzed with chilled water (100ml), and extracted with diethyl ether (3×100ml). The combined extracts were dried with magnesium sulphate and concentrated to give crystals of 2-bromoindan-1-ol upon standing overnight at -24C. The obtained 2-bromoindan-1-ol (120mmol) was suspended in 100ml of toluene and mixed with a catalytic amount of para-toluenesulfonic acid monohydrate. The mixture was heated at reflux for 12h, and water was removed by a Dean-Stark apparatus. The resulting dark brown suspension was filtered and the volatiles were removed under vacuum. The residue was passed through silica gel using pentane as eluent, then the solvent was evaporated, and the crude product was distilled in vacuo. 2-Bromoindene was finally obtained as yellow crystals in 55% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With trisodium thiophosphate In N,N-dimethyl-formamide for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With N-Bromosuccinimide for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With methanol; N-Bromosuccinimide for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium molybdate; dihydrogen peroxide; potassium bromide In chloroform; water at 25℃; for 24h; Yield given. Yields of byproduct given; | ||
With sodium molybdate; dihydrogen peroxide; potassium bromide In chloroform; water at 25℃; for 4h; Yield given. Yields of byproduct given; | ||
1: 80 %Chromat. 2: 20 %Chromat. | With ammonium metavanadate; perchloric acid; tetrabutylammomium bromide; dihydrogen peroxide In chloroform; water at 20℃; for 0.583333h; | General bromination with TBAB General procedure: NH4VO3 (5 mol%) and H2O2 (200 mol%) were placed in a flask. After complete dissolution of the catalyst, TBAB (3 mmol) was added and the mixture was stirred at room temperature. Then, Et2O (10 ml) and aromatic substrate (1 mmol) were added to the mixture. Finally, by slow drip, 1 ml of 1N HClO4 solution was added. After adding the acid, the colour of the reaction changed from yellow to red due to the formation of oxomonoperoxovanadium. Conversion was followed by TLC and determined by GC. The phases were separated and the aqueous phase was extracted with CH2Cl2 (15 ml x3). The organic phases were pooled, washed with brine, dried over Na2SO4 and filtered. The solvent was removed under reduced pressure and the resulting crude product was purified by column chromatography with Hex:AcOEt. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80 - 90℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 2℃; sowie bei 90grad; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 2℃; sowie bei 90grad; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Rk.mit K2Cr2O7 -> 2-Bromindanon; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetone | ||
With acetone; magnesium carbonate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
nachfolgend Kochen mit verd. Schwefelsaeure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 50 - 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol; ammonia |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 47 percent / p-toluenesulfonic acid / toluene / 2 h / Heating 2: 51 percent / sodium carbonate; tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium bicarbonate / methanol 2: water / ethanol / 24 h / Beauveria sulfurescens |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium bicarbonate / methanol 2: water / ethanol / 24 h / Beauveria sulfurescens |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium bicarbonate / methanol 2: 14 percent / dil. sulfuric acid / tetrahydrofuran / 24 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium bicarbonate / methanol 2: 75 percent / dil. sulfuric acid / tetrahydrofuran / 24 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium bicarbonate / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 65 percent / H2SO4 / toluene / 1 h / Heating 2: 38 percent / aq NaOH / CHCl3 / 1.) RT, 2 h, 2.) reflux, 8 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 65 percent / H2SO4 / toluene / 1 h / Heating 2: 38 percent / aq NaOH / CHCl3 / 1.) RT, 2 h, 2.) reflux, 8 h 3: 1.) n-butyllithium / 1.) THF, -70 deg C, 45 min, 2a.) -70 deg C, 45 min, 2b.) RT, 12 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 65 percent / H2SO4 / toluene / 1 h / Heating 2: 38 percent / aq NaOH / CHCl3 / 1.) RT, 2 h, 2.) reflux, 8 h 3: 1.) n-butyllithium / 1.) THF, -70 deg C, 45 min, 2a.) -70 deg C, 45 min, 2b.) RT, 12 h 4: 97 percent / tetrahydrofuran; benzene; diethyl ether / 1 h / -70 °C 5: 4.6 g / LiAlH4, AlCl3 / diethyl ether / 0.33 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 65 percent / H2SO4 / toluene / 1 h / Heating 2: 38 percent / aq NaOH / CHCl3 / 1.) RT, 2 h, 2.) reflux, 8 h 3: 1.) n-butyllithium / 1.) THF, -70 deg C, 45 min, 2a.) -70 deg C, 45 min, 2b.) RT, 12 h 4: 97 percent / tetrahydrofuran; benzene; diethyl ether / 1 h / -70 °C 5: 4.6 g / LiAlH4, AlCl3 / diethyl ether / 0.33 h / Heating 6: N-methylpyrrolidinone / 24 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 65 percent / H2SO4 / toluene / 1 h / Heating 2: 38 percent / aq NaOH / CHCl3 / 1.) RT, 2 h, 2.) reflux, 8 h 3: 1.) n-butyllithium / 1.) THF, -70 deg C, 45 min, 2a.) -70 deg C, 45 min, 2b.) RT, 12 h 4: 97 percent / tetrahydrofuran; benzene; diethyl ether / 1 h / -70 °C 5: 4.6 g / LiAlH4, AlCl3 / diethyl ether / 0.33 h / Heating 6: N-methylpyrrolidinone / 24 h / Heating 7: 90 percent / KOH / bis-(2-hydroxy-ethyl) ether / 22 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 65 percent / H2SO4 / toluene / 1 h / Heating 2: 38 percent / aq NaOH / CHCl3 / 1.) RT, 2 h, 2.) reflux, 8 h 3: 1.) n-butyllithium / 1.) THF, -70 deg C, 45 min, 2a.) -70 deg C, 45 min, 2b.) RT, 12 h 4: 97 percent / tetrahydrofuran; benzene; diethyl ether / 1 h / -70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: diluted Cr2O3-H2SO4 / 50 - 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrazine hydrate / 140 °C 2: diluted acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrazine hydrate / 140 °C 2: d-tartaric acid; alcohol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrazine hydrate / 140 °C 2: d-tartaric acid; alcohol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 86% 2: 10% 3: 1% | With sodium bromate; sulfuric acid; sodium bromide In 1,4-dioxane; water at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / diethyl ether / 12 h / 20 °C 2: C56H61O4P / (2)H8-toluene / -50 °C / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / diethyl ether / 12 h / 20 °C 2: (R)-3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 20 h / 90 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / Dimethyl ether; water / 6 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 20 h / 90 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / Dimethyl ether; water / 6 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / toluene / 20 h / 90 °C 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / Dimethyl ether; water / 6 h / 90 °C / Inert atmosphere 3.1: n-butyllithium / toluene; tetrahydrofuran / 24 h / 0 - 20 °C 3.2: 24 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / toluene / 20 h / 90 °C 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / Dimethyl ether; water / 6 h / 90 °C / Inert atmosphere 3.1: n-butyllithium / toluene; tetrahydrofuran / 24 h / 0 - 20 °C 3.2: 24 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 72 h / Reflux; Dean-Stark 2: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / diethyl ether / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / toluene / 12 h / Inert atmosphere; Schlenk technique; Reflux 2.1: magnesium / tetrahydrofuran / 4.67 h / Inert atmosphere; Schlenk technique; Reflux 2.2: 12 h / Inert atmosphere; Schlenk technique; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / toluene / 12 h / Inert atmosphere; Schlenk technique; Reflux 2.1: magnesium / tetrahydrofuran / 4.67 h / Inert atmosphere; Schlenk technique; Reflux 2.2: 12 h / Inert atmosphere; Schlenk technique; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / toluene / 12 h / Inert atmosphere; Schlenk technique; Reflux 2.1: magnesium / tetrahydrofuran / 4.67 h / Inert atmosphere; Schlenk technique; Reflux 2.2: 12 h / Inert atmosphere; Schlenk technique; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0℃; for 2.5h; | 1-1 1-1, Synthesis of 2-bromo-2,3-dihydro-1H-inden-1-yl methanesulfonic acid 2-Bromo-2,3-dihydro-1H-inden-1-ol (10 · 0 g, 46 · 93 mmol), triethylamine (10.8 g, 106.73 mmol) in DCM (50 mL) Methanesulfonyl chloride MsCl (9.9 g, 86.43 mmol) was added dropwise to the solution, and the addition was completed over 30 minutes. The mixture was stirred for a further 2 hours and then allowed to warm to room temperature. Water (50 mL) was added, the DCM layer was separated and the aqueous phase was extracted twice with DCM (2×30mL). The combined organic phases were washed with brine (50 mL) then dried over Na2EtOAc. The solvent was removed in vacuo to give 2-bromo-2,3-dihydro-1H-indol-1-yl methanesulfonic acid as a crude oil (yield: 13.53 g, yield: 99%) and the product was used directly in the next step without further purification. | |
With triethylamine In dichloromethane at 20℃; for 2.5h; | 1.1-1 1-1, Synthesis of 2-bromo-2,3-dihydro-1H-inden-1-yl methanesulfonic acid: To a solution of 2-bromo-2,3-dihydro-1H-inden-1-ol (10.0 g, 46.93 mmol), triethylamine (10.8 g, 106.73 mmol) in DCM (50 mL) Methanesulfonyl chloride MsCl (9.9 g, 86.43 mmol) was added dropwise over 30 minutes. The mixture was stirred for a further 2 hours and then allowed to warm to room temperature. Water (50 mL) was added, the DCM layer was separated and the aqueous phase was extracted twice with DCM (2×30mL). The combined organic phases were washed with brine (50 mL) then dried over Na2EtOAc.The solvent was removed in vacuo to give 2-bromo-2,3-dihydro-1H-indol-1-yl methanesulfonic acid as a crude oil (yield: 13.53 g, yield: 99%). Used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 2.5 h / 0 °C 2: hydroxylamine hydrochloride; triethylamine / dichloromethane / 2 h / Reflux 3: hydrogenchloride / water / 6 h / 5 - 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2.5 h / 0 °C 2: hydroxylamine hydrochloride; triethylamine / dichloromethane / 2 h / Reflux 3: hydrogenchloride / water / 6 h / 5 - 40 °C | ||
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2.5 h / 20 °C 2: triethylamine; hydroxylamine hydrochloride / dichloromethane / 2 h / Reflux 3: hydrogenchloride / water / 6 h / 5 - 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2.5 h / 0 °C 2: hydroxylamine hydrochloride; triethylamine / dichloromethane / 2 h / Reflux | ||
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2.5 h / 20 °C 2: triethylamine; hydroxylamine hydrochloride / dichloromethane / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 2.5 h / 20 °C 2: triethylamine; hydroxylamine hydrochloride / dichloromethane / 2 h / Reflux 3: hydrogenchloride / water / 6 h / 5 - 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 2.5 h / 20 °C 2: triethylamine; hydroxylamine hydrochloride / dichloromethane / 2 h / Reflux 3: hydrogenchloride / water / 6 h / 5 - 40 °C 4: potassium carbonate; palladium / water; ethanol / 0.17 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 2.5 h / 20 °C 2: triethylamine; hydroxylamine hydrochloride / dichloromethane / 2 h / Reflux 3: hydrogenchloride / water / 6 h / 5 - 40 °C 4: potassium carbonate; palladium / water; ethanol / 0.17 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 2.5 h / 20 °C 2: triethylamine; hydroxylamine hydrochloride / dichloromethane / 2 h / Reflux 3: hydrogenchloride / water / 6 h / 5 - 40 °C 4: potassium carbonate; palladium / water; ethanol / 0.17 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 2.5 h / 20 °C 2: triethylamine; hydroxylamine hydrochloride / dichloromethane / 2 h / Reflux 3: hydrogenchloride / water / 6 h / 5 - 40 °C 4: potassium carbonate; palladium / water; ethanol / 0.17 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With sodium sulfide hydrate; Aliquat 336 for 4h; Reflux; | 2 2,2'-Thiodiindan-l-ol. A mixture of 55.1 g (259 mmol) 2-bromoindan-l-ol, 37.5 g (156 mmol) of sodium sulfide nonahydrate, and 1.88 g (5.00 mmol) of trioctyl methylammonium chloride in 1,000 ml of water was refluxed for 4 hours. After cooling to room temperature, the resulting mixture was extracted with dichloromethane (3 x 500 ml). The combined organic extract was washed with water (2 x 200 ml), dried over Na2SO4, and then evaporated to dryness. The residue was washed with 30 ml of ethanol and then dried in vacuo. Yield 19.3 g (50%) of a white solid. 1H NMR (DMSO-d6, 400 MHz): d 7.26-7.34 (m, 2H), 7.10-7.27 (m, 6H), 5.38 (d, 7 = 4.1 Hz, 1 H), 5.29 (d, 7= 4.4 Hz, 1 H), 4.46 (m, 1 H), 4.36 (ddd, J= 9.7, 3.7, 3.4 Hz, 1 H), 4.23 (d, J= 3.1 Hz, 1 H), 4.13 (d, J= 3.1 Hz, 1 H), 3.21 (dt, J= 16.2, 6.7 Hz, 2 H), 2.72 (dd, J= 6.4, 3.6 Hz, 1 H), 2.67 (dd, J= 6.4, 3.6 Hz, 1 H). |
Tags: 5400-80-6 synthesis path| 5400-80-6 SDS| 5400-80-6 COA| 5400-80-6 purity| 5400-80-6 application| 5400-80-6 NMR| 5400-80-6 COA| 5400-80-6 structure
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