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CAS No. : | 57807-28-0 | MDL No. : | MFCD11109720 |
Formula : | C9H9Br | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DTUGHJZKCKSVEO-UHFFFAOYSA-N |
M.W : | 197.07 | Pubchem ID : | 12221356 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
Under nitrogen atmosphere, under ice-cooling, diethylzinc 20 ml (1.0M hexane solution) was dissolved in dichloromethane 20 ml and thereto was added a solution of trifluoroacetic acid 2.28 g in dichloromethane 20 ml. The resulting mixture solutions were stirred under ice-cooling for 20 minutes and thereto was added a solution of diiodomethane 5.36 g in dichloromethane 20 ml and the resulting mixtures were stirred for 20 minutes. To resulting solutions was added a solution of 2-bromostyrene 1.83 g in dichloromethane 10 ml under ice-cooling and the resulting mixtures were stirred at RT for 6 hours. To the resulting reaction solutions was added 2N hydrochloric acid to make the mixtures pH 1 to 2 and then the resulting mixtures were extracted with hexane. The organic layers were washed with saturated saline, dried over anhydrous magnesium sulfate and filtered, and the resulting filtrates were concentrated under reduced pressure to give the compound of the formula (32-4) 1.76 g as crude products. [0983] 1H NMR (CDCl3) [0984] delta ppm: 7.54 (1H, dd), 7.20 (1H, td), 7.02 (1H, td), 6.93 (1H, dd), 2.16 (1H, tt), 1.01 (2H, ddd), 0.68 (2H, dt) | ||
Production Example 1-43 Production of Compound Represented by Formula (1-102) Production of Compound Represented by Formula 32-4 20 ml of diethyl zinc (1.0M hexane solution) was dissolved in 20 ml of dichloromethane under ice-cooling in a nitrogen atmosphere, and a solution of 2.28 g of trifluoroacetic acid in 20 ml of dichloromethane was added thereto. The obtained mixed liquid was stirred for 20 minutes under ice-cooling, and a solution of 5.36 g of diiodomethane in 20 ml of dichloromethane was added thereto, followed by stirring for 20 minutes. A solution of 1.83 g of 2-bromostyrene in 10 ml of dichloromethane was added to the obtained solution under ice-cooling, followed by stirring at room temperature for 6 hours. The obtained reaction liquid was controlled to have a pH of 1 to 2 by adding 2 N hydrochloric acid water, and the resultant product was extracted with hexane. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and filtered, and the obtained filtrate was concentrated under reduced pressure, whereby 1.76 g of a crude product of the compound represented by Formula (32-4) was obtained. (1195) 1H NMR (CDCl3) (1196) delta (1197) ppm: 7.54 (1H, dd), 7.20 (1H, td), 7.02 (1H, td), 6.93 (1H, dd), 2.16 (1H, tt), 1.01 (2H, ddd), 0.68 (2H, dt) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 7 -bromocvclopropylbenzeneA 12-L 4-neck round bottom flask equipped with a mechanical stirrer, a thermocouple, a dropping funnel, and nitrogen inlet adapter was charged with cyclopropylbenzene (150.0 g, 1 .23 mol) and CH2CI2 (1 .5 L). The resulting solution was cooled to -76°C with stirring. Bromine (65.4 ml_, 1 .26 mol) in CH2CI2 (0.75 L) was added slowly dropwise over a 2-h period and the resulting mixture was stirred at -76°C for 3 h. The resulting mixture was then warmed to -20°C (in an ice-water bath), saturated aqueous NaHC03 solution (2.0 L) was added and the mixture was stirred for 10 min. After phase separation, the organic phase was washed with brine (1 .0 L) and concentrated at 40°C under house vacuum (then 20 mmHg for 2 min) to yield a mixture of A:4- bromocyclopropylbenzene; B:2-bromocyclopropylbenzene; C:2,4- dibromocyclopropylbenzene; and D:cyclorporpylbenzene.The mixture was purified by distillation with a short-path distillation head and KNF Diaphragm pump, to yield the following four fractions under the given conditions. Fractions F2 and F3 were used for the preparation of Gringard reagent as described in Example 8 which follows.Collection Conditions(head temp °C/pot A/B/C/DFraction temp °C/mmHg) (HPLC areapercent) Physical Form30-55°C / 80-90°C /F1 6 mm Hg 26/0.0/0.3/74 A colorless oil.70-80°C / 91 -100°C /F2 5-6 mm Hg 93/0.0/1 .9/5.1 A colorless oil80-60°C / 100-1 10°C /F3 5-6 mm Hg 96/0.0/3.6/0.0 A colorless oil 0°C / >1 10°C /PT 5-6 mm Hg 15/31/51 (?)/0.0 A yellowish oil1 H NMR (D SO-cfe, 300 MHz) delta 7.48 (d, J = 7.9 Hz, 2 H), 6.97 (d, J = 8.0 Hz, 2 H), 1 .85 (m, 1 H), 0.94 (m, 2 H), 0.62 (m, 2 H)13C NMR (DMSO-cfe, 75.47 MHz) 143.1 , 130.9 (2 C), 127.4 (2 C), 1 18.0, 14.6, 9.42 (2 C)LC-MS mlz MH+ = 197, 199 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Under nitrogen atmosphere, at RT, the compound of the formula (32-4) 1.76 g was dissolved in tetrahydrofuran 9 ml. The resulting solutions were cooled to ?78° C. and thereto added n-butyllithium 6.6 ml (1.6M hexane solution) and the resulting mixtures were stirred for 30 minutes. Thereafter, to the resulting mixtures was added a suspension of trichlorobismuth 939 mg in tetrahydrofuran 5 ml and the resulting mixtures were stirred for 1 hour with heating to rt. To the resulting reaction solutions was added water 20 ml and the resulting mixtures were extracted with chloroform. The resulting chloroform layers were washed with saturated saline, dried over anhydrous magnesium sulfate and then filtered, and the resulting filtrates were concentrated under reduced pressure to give the compound of the formula (33-4) 2.27 g as crude products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Production of Compound Represented by Formula 31-4 1.76 g of the compound represented by Formula (32-4) was dissolved in 9 ml of tetrahydrofuran at room temperature in a nitrogen atmosphere. The obtained solution was cooled to ?78° C., and 6.6 ml of n-butyllithium (1.6 M hexane solution) was added thereto, followed by stirring for 30 minutes. Next, a suspension of 939 mg of trichlorobismuth in 5 ml of tetrahydrofuran was added to the obtained mixture, followed by stirring for 1 hour while heating to room temperature. 20 ml of water was added to the obtained reaction liquid, and the resultant product was extracted with chloroform. The obtained chloroform layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and filtered, and the obtained filtrate was concentrated under reduced pressure, whereby 2.27 g of a crude product of the compound represented by Formula (33-4) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃; for 16h;Inert atmosphere; | Step 2. 2-(2-Cyclopropylphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (0802) [00254] A mixture of l-bromo-2-cyclopropylbenzene (11.00 g, 55.82 mmol), Pd(dppf)Cl2 CH2CI2 (4.56 g, 5.58 mmol), potassium acetate (16.43 g, 167.45 mmol), 4,4,5,5- tetramethyl-2-(tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (17.01 g, 66.98 mmol) and 1,4-dioxane (500 mL) was stirred for 16 h at 90 °C under an atmosphere of nitrogen. After cooling to ambient temperature, the reaction mixture was poured into water (200 mL) and was extracted with EtOAc (3 x 200 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (eluting with 0percent to 0.1percent EtOAc/PE), the product was further purified by C18- reversed phase silica gel chromatography (eluting 5percent to 100percent acetonitrile/aqueous Sodium hydrideCC solution (10 mmol)). This resulted in 6.1 g (44percent) of 2-(2-cyclopropylphenyl)- 4,4,5,5-tetramethyl-l,3,2-dioxaborolane as a yellow oil. 1H NMR (400 MHz, CD3OD) delta 7.70- 7.63 (m, 1H), 7.37-7.19 (m, 1H), 7.18-7.06 (m, 1H), 6.91-6.81 (m, 1H), 2.74-2.62 (m, 1H), 1.38- 1.35 (m, 12H), 1.00-0.89 (m, 2H), 0.72-0.60 (m, 2H). MS (ESI) m/z 244.9 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 60℃; for 16h;Inert atmosphere; | Step 1. 3-Fluoro-2-(prop-l-en-2-yl)phenol (0764) [00242] A mixture of 2-bromo-3-fluorophenol (2 g, 10.47 mmol), 4,4,5, 5-tetramethyl-2-(prop- l-en-2-yl)-l,3,2-dioxaborolane (1.95 g, 11.60 mmol), Pd(dppf)Cl2 CH2C12 (858 mg, 1.05 mmol), potassium carbonate (2.90 g, 21.00 mmol), water (4 mL) and 1,4-dioxane (20 mL) was stirred for 16 h at 60 °C under an atmosphere of nitrogen. After cooling to ambient temperature, the reaction mixture was concentrated under vacuum and the residue was purified by silica gel chromatography eluting with EtOAc/PE (1 :2) to afford 500 mg (31percent) of 3-fluoro-2-(prop-l-en- 2-yl)phenol as light brown oil. MS (ESI) m/z 153 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.8 g | To the solution of 1-bromo-2-cyclopropylbenzene (8.5 g, 0.043 mol) in THF (20 mL) was added n-BuLi (21 mL, 0.052 mol, 2.5M in hexane) at -78 C under N 2 atmosphere. Then the mixture was stirred at -78C for 1 hour. To the solution of tetrahydrocyclopenta [c] pyrrole-1, 3 (2H, 3aH) -dione (4 g, 0.029 mol) in THF (20 mL) was added n-BuLi (13 mL, 0.035 mol, 2.5M in hexane) at -78C under N 2 atmosphere. Then the mixture was stirred at 0C for 1 hour. The solution formed from 1-bromo-2-cyclopropylbenzene was added dropwise to the solution formed from tetrahydrocyclopenta [c] pyrrole-1, 3 (2H, 3aH) -dione at -78C. The resulting mixture was stirred at room temperature for 3 hours. TLC showed tetrahydrocyclopenta [c] pyrrole-1, 3 (2H, 3aH) -dione was consumed. NaBH 3CN (2.2 g, 0.035 mol) was added to the mixture and then followed by addition of 6N HCl acid (20 mL) at 0C, and further stirred at room temperature for 1 hour. Na 2CO 3 (50 mL) was added to the mixture to adjust the pH to 8-9. The mixture was then extracted with EA (50 mL 3), and the organic layer was washed with brine (50 mL 2). The combined organic layer was dried, filtered and concentrated. The residue was purified by column chromatograph on silica gel (eluent: PE/EA = 10/1) to obtain 3- (2-cyclopropylphenyl) hexahydrocyclopenta [c] pyrrol-1 (2H) -one (2.8 g). 1H NMR (400MHz, CDCl 3) delta ppm: 7.19-7.23 (m, 1H), 7.11-7.16 (m, 2H), 6.95-7.01 (m, 1H), 6.20 (s, 1H), 5.44 (d, J=7.7 Hz, 1H), 3.08-3.24 (m, 1H), 2.93-3.04 (m, 1H), 2.73-2.87 (m, 1H), 1.91-2.06 (m, 1H), 1.73-1.83 (m, 2H), 1.51-1.64 (m, 1H), 1.40-1.49 (m, 2H), 1.33 (s, 1H), 1.10-1.20 (m, 1H), 0.52-0.73 (m, 2H). MS (ESI, m/e) [M+1] + 242.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: 1-bromo-2-cyclopropylbenzene With iodine; magnesium In tetrahydrofuran at 70℃; for 1h; Inert atmosphere; Stage #2: 4-methoxypyridine; benzyl chloroformate In tetrahydrofuran at -20℃; for 1h; | 1 Step 1: benzyl 2- (2-cyclopropylphenyl) -4-oxo-3, 4-dihydropyridine-1 (2H) -carboxylate A small amount of I2(10 mg, catalyst) was added to the solution of Mg (0.9 g, 38 mmol) in THF (20 mL) at 25 under N2, then 1-bromo-2-cyclopropylbenzene (5.0 g, 25 mmol) was added in drops. The mixture was heated to 70 for 1 hr until the brown color disappeared. The solution of Grignard Reagent was added dropwise to the pyridinium salt obtained from 4-methoxypyridine (1.85 g, 0.017 mol) and benzyl carbonochloridate (3.2 mL, 0.022 mol) in dry THF (50 mL) at -20 . The mixture was stirred at -20 for 1 hr. The HCl (1 M, 50 mL) was added to the mixture, extracted with EtOAc (20 mL ×3) . The combined organic phases were washed with brine (20 mL*2) , dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (silica gel, eluent: PE/EA (v/v) = 10/1) to give benzyl 2- (2-cyclopropylphenyl) -4-oxo-3, 4-dihydropyridine-1 (2H) -carboxylate (4.0 g, yield: 68%) as a brown oil. 1H NMR (400 MHz, CDCl3) δ ppm: 8.20 (d, J=8.4 Hz, 1H) , 7.40-7.27 (m, 3H) , 7.21-7.08 (m, 5H) , 6.26 (br d, J= 8.8 Hz, 1H) , 5.47 (d, J= 8.4 Hz, 1H) , 5.20-5.11 (m, 2H) , 3.23-3.17 (m, 1H) , 2.72 (d, J= 16.4 Hz, 1H) , 1.80 (br s, 1H) , 0.98-0.83 (m, 2H) , 0.72-0.49 (m, 2H) . |
Tags: 57807-28-0 synthesis path| 57807-28-0 SDS| 57807-28-0 COA| 57807-28-0 purity| 57807-28-0 application| 57807-28-0 NMR| 57807-28-0 COA| 57807-28-0 structure
[ 57190-17-7 ]
2-Bromo-1,3-diisopropylbenzene
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[ 21524-34-5 ]
2-Bromo-1,3,5-triisopropylbenzene
Similarity: 0.90
[ 57190-17-7 ]
2-Bromo-1,3-diisopropylbenzene
Similarity: 0.90
[ 21524-34-5 ]
2-Bromo-1,3,5-triisopropylbenzene
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