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CAS No. : | 1435-51-4 | MDL No. : | MFCD00061119 |
Formula : | C6H3Br2F | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ASWYHZXKFSLNLN-UHFFFAOYSA-N |
M.W : | 253.89 | Pubchem ID : | 137003 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.8 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.07 cm/s |
Log Po/w (iLOGP) : | 2.42 |
Log Po/w (XLOGP3) : | 3.92 |
Log Po/w (WLOGP) : | 3.77 |
Log Po/w (MLOGP) : | 4.22 |
Log Po/w (SILICOS-IT) : | 3.64 |
Consensus Log Po/w : | 3.59 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.38 |
Solubility : | 0.0107 mg/ml ; 0.000042 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.62 |
Solubility : | 0.061 mg/ml ; 0.00024 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.38 |
Solubility : | 0.0105 mg/ml ; 0.0000412 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.53 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
95% | at 20℃; | To a 500 mL round bottom flask was added 3,5-dibromofluorobenzene (8) (20.0 g, 0.08 mol, 1 eq.) And anhydrous DMF (350 mL). To a round bottom flask was slowly added sodium methoxide (5.2 g , 0.09 mol, 1.2 eq.), Stir at room temperature overnight, Then add 5percent HCl to neutralize, Stop the reaction. CH2Cl2 extraction (50 mL x 3), The organic phase was washed with distilled water (50 mL x 3) The organic phase was dried over anhydrous magnesium sulfate, The magnesium sulfate was removed by filtration, The solvent was removed by flash evaporation to give a pale yellow solid, Silica gel column chromatography (eluent: petroleum ether), A white solid was obtained 30 g, Yield 95percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With pyridine In N,N-dimethyl-formamide for 3 h; Reflux | Example 14 3-Bromo-5-fluorobenzonitrile A 250-mL round-bottom flask equipped with a magnetic stir bar was charged with 1,3-dibromo-5-fluorobenzene (7.70 g, 30.3 mmol), DMF (45 mL), pyridine (4.9 mL), and copper (I) cyanide (2.72 g, 30.3 mmol) under nitrogen. A reflux condenser was attached to the flask. The green, cloudy mixture was stirred at reflux for 3 h. Once lower Rf impurities were observed, the reaction was allowed to cool to room temperature. The reaction was quenched with 30 mL of ether, and a precipitate formed in the dark solution. The precipitate was gravity-filtered though Celite. The filtrate was rinsed three times with ether (100 mL/50 g bromide). The isolated solution was added to a separatory funnel. The organic layer was washed with a 2:1 mixture of water and concentrated ammonium hydroxide (30 mL), followed by saturated ammonium chloride solution (2*30 mL) and saturated sodium bicarbonate (30 mL). The aqueous layers were extracted with ether (3*40 mL). The organic layers were combined and dried over anhydrous sodium sulfate. The product was purified by flash column chomatography to yield 3-bromo-5-fluorobenzonitrile (2.10 g, 35percent). 1H NMR (400 MHz, CDCl3) δ 7.62 (s, 1H), 7.54-7.50 (m, 1H), 7.35-7.32 (m, 1H). |
35% | With pyridine In N,N-dimethyl-formamide for 3 h; Reflux; Inert atmosphere | Example 14 3-Bromo-5-fluorobenzonitrile A 250-mL round-bottom flask equipped with a magnetic stir bar was charged with 1,3-dibromo-5-fluorobenzene (7.70 g, 30.3 mmol), DMF (45 mL), pyridine (4.9 mL), and copper (I) cyanide (2.72 g, 30.3 mmol) under nitrogen. A reflux condenser was attached to the flask. The green, cloudy mixture was stirred at reflux for 3 h. Once lower Rf impurities were observed, the reaction was allowed to cool to room temperature. The reaction was quenched with 30 mL of ether, and a precipitate formed in the dark solution. The precipitate was gravity-filtered though Celite. The filtrate was rinsed three times with ether (100 mL/50 g bromide). The isolated solution was added to a separatory funnel. The organic layer was washed with a 2:1 mixture of water and concentrated ammonium hydroxide (30 mL), followed by saturated ammonium chloride solution (2*30 mL) and saturated sodium bicarbonate (30 mL). The aqueous layers were extracted with ether (3*40 mL). The organic layers were combined and dried over anhydrous sodium sulfate. The product was purified by flash column chomatography to yield 3-bromo-5-fluorobenzonitrile (2.10 g, 35percent). 1H NMR (400 MHz, CDCl3) δ 7.62 (s, 1H), 7.54-7.50 (m, 1H), 7.35-7.32 (m, 1H). |
35% | With pyridine In N,N-dimethyl-formamide for 3 h; Inert atmosphere; Reflux | Example 14 3-Bromo-5-fhiorobenzonitrileA 250-mL round-bottom flask equipped with a magnetic stir bar was charged with 1,3- dibromo-5-fluorobenzene (7.70 g, 30.3 mmol), DMF (45 mL), pyridine (4.9 mL), and copper (I) cyanide (2.72 g, 30.3 mmol) under nitrogen. A reflux condenser was attached to the flask. The green, cloudy mixture was stirred at reflux for 3 h. Once lower Rf impurities were observed, the reaction was allowed to cool to room temperature. The reaction was quenched with 30 mL of ether, and a precipitate formed in the dark solution. The precipitate was gravity- filtered though Celite. The filtrate was rinsed thee times with ether (100 mL/50 g bromide). The isolated solution was added to a separatory funnel. The organic layer was washed with a 2:1 mixture of water and concentrated ammonium hydroxide (30 mL), followed by saturated ammonium chloride solution (2 x 30 mL) and saturated sodium bicarbonate (30 mL). The aqueous layers were extracted with ether (3 x 40 mL). The organic layers were combined and dried over anhydrous sodium sulfate. The product was purified by flash column chomatography to yield 3-bromo-5-fluorobenzonitrile (2.1O g, 35percent). 1H NMR (400 MHz, CDCl3) δ 7.62 (s, 1 H), 7.54-7.50 (m, 1 H), 7.35-7.32 (m, 1 H). |
23% | With pyridine In N,N-dimethyl-formamide at 150℃; for 4.5 h; Inert atmosphere | A mixture of 1,3-dibromo-5-fluorobenzene (7.4 g, 29.3 mmol), copper(I) cyanide (2.6 g, 29.3 mmol), pyridine (3 mL) and N,N-dimethylformamide (30 mL) under an argon atmosphere was heated to 150 °C for 4.5 h. Mixture was allowed to room temperature, diethyl ether (100 mL) was added and the formed precipitate was removed via filtration, the precipitate was washed with diethyl ether (100 mL), the filtrate was washed consecutively with: 1) 10 percent ammonium hydroxide (100 mL), 2) saturated ammonium chloride (100 mL), and 3) saturated sodium bicarbonate (100 mL), dried over magnesium sulfate and evaporated. Purification of the residue by flash chromatography, using a stepwise gradient of heptane to heptane:ethyl acetate 9:1 afforded the title compound (1.3 g, 23percent). 1H NMR (400 MHz, CDCl3) d ppm 7.30 - 7.37 (m, 1 H), 7.48 (dt, J=7.83, 1.89 Hz, 1 H), 7.58 (s, 1 H); 13C NMR (101 MHz, CDCl3) d 115.5, 115.6, 116.4, 116.5, 118.5, 118.7, 123.9, 124.0, 124.4, 124.7, 131.4, 131.4, 161.1, 163.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With pyridine; ammonium hydroxide; ammonium chloride; sodium hydrogencarbonate In water; N,N-dimethyl-formamide | 3-Bromo-5-fluorobenzonitrile To a 1 liter r.b. flask equivuipped with a magnetic stir bar, commercially available 1,3-dibromo-5-fluorobenzene (44.0 g, 173.3 mmol), DMF (268 mL), pyridine (28.0 mL), and copper (I) cyanide (15.5 g, 173.3 mmol) were added under nitrogen. A reflux condenser was attached to the flask. The green cloudy mixture was stirred at reflux for 3 h. The reaction progress was difficult to monitor by TLC, so once lower Rf impurities were observed the reaction was allowed to cool to rt. The reaction mixture was quenched with 200 mL ether which formed a precipitate in the dark solution. The precipitate was gravity filtered through Celite. The filtrate was rinsed three times with ether (100 mL). The isolated solution was added to a separatory funnel. The organic layer was washed with 2 to 1 mixture of water and ammonium hydroxide (200 mL) followed by saturated ammonium chloride solution (2*200 mL) and saturated sodium bicarbonate (200 mL). The aqueous layers were extracted with ether (3*100 mL). The organic layers were combined and dried (Na2 SO4). The product, 3-bromo-5-fluorobenzonitrile, was purified by flash column chromatography (300 mL silica, hexane) followed by re, crystallization from hexane to afford 22.3 g (65percent) of the product as white crystals. Data for 3-bromo-5-fluorobenzonitrile: 1 H NMR (400 MHz, acetone-d6) 7.81 (s, 1H), 7.73 (dd, J=8.4, 1.9, 1H), 7.65 (dd, J=8.5, 2.0, 1H). |
65% | With pyridine; ammonium hydroxide; ammonium chloride; sodium hydrogencarbonate In water; N,N-dimethyl-formamide | 3-Bromo-5-fluorobenzonitrile To a 1 liter r.b. flask equivuipped with a magnetic stir bar, commercially available 1,3-dibromo-5-fluorobenzene (44.0 g, 173.3 mmol), DMF (268 mL), pyridine (28.0 mL), and copper (I) cyanide (15.5 g, 173.3 mmol) were added under nitrogen. A reflux condenser was attached to the flask. The green cloudy mixture was stirred at reflux for 3 h. The reaction progress was difficult to monitor by TLC, so once lower Rf impurities were observed the reaction was allowed to cool to rt. The reaction mixture was quenched with 200 mL ether which formed a precipitate in the dark solution. The precipitate was gravity filtered through Celite. The filtrate was rinsed three times with ether (100 mL). The isolated solution was added to a separatory funnel. The organic layer was washed with 2 to 1 mixture of water and ammonium hydroxide (200 mL) followed by saturated ammonium chloride solution (2*200 mL) and saturated sodium bicarbonate (200 mL). The aqueous layers were extracted with ether (3*100 mL). The organic layers were combined and dried (Na2 SO4). The product, 3-bromo-5-fluorobenzonitrile, was purified by flash column chromatography (300 mL silica, hexane) followed by recrystallization from hexane to afford 22.3 g (65percent) of the product as white crystals. Data for 3-bromo-5-fluorobenzonitrile: 1 H NMR (400 MHz, acetone-d6) 7.81 (s, 1 H), 7.73 (dd, J=8.4, 1.9, 1 H), 7.65 (dd, J=8.5, 2.0, 1 H). |
65 % | With pyridine; ammonium hydroxide; ammonium chloride; sodium hydrogencarbonate In water; N,N-dimethyl-formamide | EXAMPLE 171 6-(3-Cyano-5-fluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 271, structure 4 of Scheme II, where R1 =-cyano-5-fluorophenyl) 3-Bromo-5-fluorobenzonitrile. To a 1 liter r.b. flask equivuipped with a magnetic stir bar, commercially available 1,3-dibromo-5-fluorobenzene (44.0 g, 173.3 mmol), DMF (268 mL), pyridine (28.0 mL), and copper (I) cyanide (15.5 g, 173.3 mmol) were added under nitrogen. A reflux condenser was attached to the flask. The green cloudy mixture was stirred at reflux for 3 h. The reaction progress was difficult to monitor by TLC, so once lower Rf impurities were observed the reaction was allowed to cool to rt. The reaction mixture was quenched with 200 mL ether which formed a precipitate in the dark solution. The precipitate was gravity filtered through Celite. The filtrate was rinsed three times with ether (100 mL). The isolated solution was added to a separatory funnel. The organic layer was washed with 2 to 1 mixture of water and ammonium hydroxide (200 mL) followed by saturated ammonium chloride solution (2*200 mL) and saturated sodium bicarbonate (200 mL). The aqueous layers were extracted with ether (3*100 mL). The organic layers were combined and dried (Na2 SO4). The product, 3-bromo-5-fluorobenzonitrile, was purified by flash column chromatography (300 mL silica, hexane) followed by recrystallization from hexane to afford 22.3 g (65 percent) of the product as white crystals. Data for 3-bromo-5-fluorobenzonitrile: 1It NMR (400 MHz, acetone-d6) 7.81 (s, 1 H), 7.73 (dd, J=8.4, 1.9, 1 H), 7.65 (dd, J=8.5, 2.0, 1 H). |
65% | With pyridine; ammonium hydroxide; ammonium chloride; sodium hydrogencarbonate In water; N,N-dimethyl-formamide | 3-Bromo-5-fluorobenzonitrile. To a 1 liter r.b. flask equivuipped with a magnetic stir bar, commercially available 1,3-dibromo-5-fluorobenzene (44.0 g, 173.3 mmol), DMF (268 mL), pyridine (28.0 mL), and copper (I) cyanide (15.5 g, 173.3 mmol) were added under nitrogen. A reflux condenser was attached to the flask. The green cloudy mixture was stirred at reflux for 3 h. The reaction progress was difficult to monitor by TLC, so once lower Rf impurities were observed the reaction was allowed to cool to rt. The reaction mixture was quenched with 200 mL ether which formed a precipitate in the dark solution. The precipitate was gravity filtered through Celite. The filtrate was rinsed three times with ether (100 mL). The isolated solution was added to a separatory funnel. The organic layer was washed with 2 to 1 mixture of water and ammonium hydroxide (200 mL) followed by saturated ammonium chloride solution (2*200 mL) and saturated sodium bicarbonate (200 mL). The aqueous layers were extracted with ether (3*100 mL). The organic layers were combined and dried (Na2 SO4). The product, 3-bromo-5-fluorobenzonitrile, was purified by flash column chromatography (300 mL silica, hexane) followed by recrystallization from hexane to afford 22.3 g (65percent) of the product as white crystals. Data for 3-bromo-5-fluorobenzonitrile: 1 H NMR (400 MHz, acetone-d6) 7.81 (s, 1 H), 7.73 (dd, J=8.4, 1.9, 1 H), 7.65 (dd, J=8.5, 2.0, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With pyridine In N,N-dimethyl-formamide for 3 h; Inert atmosphere; Reflux | Example 17 3-Bromo-5-fluorobenzonitrile A 250-mL round-bottom flask equipped with a magnetic stir bar was charged with 1,3-dibromo-5-fluorobenzene (7.70 g, 30.3 mmol), DMF (45 mL), pyridine (4.9 mL), and copper (I) cyanide (2.72 g, 30.3 mmol) under nitrogen. A reflux condenser was attached to the flask. The green, cloudy mixture was stirred at reflux for 3 h. Once lower Rf impurities were observed, the reaction was allowed to cool to room temperature. The reaction was quenched with 30 mL of ether, and a precipitate formed in the dark solution. The precipitate was gravity-filtered though Celite. The filtrate was rinsed three times with ether (100 mL/50 g bromide). The isolated solution was added to a separatory funnel. The organic layer was washed with a 2:1 mixture of water and concentrated ammonium hydroxide (30 mL), followed by saturated ammonium chloride solution (2*30 mL) and saturated sodium bicarbonate (30 mL). The aqueous layers were extracted with ether (3*40 mL). The organic layers were combined and dried over anhydrous sodium sulfate. The product was purified by flash column chromatography to yield 3-bromo-5-fluorobenzonitrile (2.10 g, 35percent). 1H NMR (400 MHz, CDCl3): δ 7.62 (s, 1H), 7.54-7.50 (m, 1H), 7.35-7.32 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | for 16 h; Heating / reflux | A mixture of 3,5-dibromofluorobenzene (3Og, 120mmol) and copper (I) cyanide (42.1 g, 470mmol) in DMF (20OmL) was heated under reflux for 16h. The reaction mixture was then concentrated In vacuo and the residue was suspended in DCM (35OmL). The resulting brown precipitate was filtered through Arbocel.(R). and the filtrate was evaporated under reduced pressure. The residue was partitioned between water (5OmL) and DCM (15OmL), and the organic layer was separated, dried over sodium sulfate and concentrated in vacuo to give a yellow solid. The solid was then dissolved in diethyl ether (40OmL), washed with water (2 x 5OmL), brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound in 52percent yield, 9.2g. m.p. = 98-100 0C. 1H NMR (400MHz, CD3OD) δ: 8.29 (m, 2H), 8.36 (m, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at 20 - 30℃; Cooling with ice; Inert atmosphere Stage #2: at 0 - 20℃; for 13.5 h; |
Ice bath, the 2M Isopropylmagnesium chloride (10 mL, 20 mmol) was dissolved in 5 mL of tetrahydrofuran, A solution of 1,3-dibromo-5-fluorobenzene 40a (4.0 g, 15.70 mmol) In tetrahydrofuran,Stirred for 2 hours, and then heated to 20 ° C reaction for 30 minutes. Cool down to 0 ° C,N, N-Dimethylformamide (2.5 mL, 31.50 mmol) was added dropwise,The reaction was stirred for 1.5 hours,The reaction was stirred at room temperature for 12 hours.The reaction was quenched by the addition of 20 mL of saturated ammonium chloride solution, extracted with ethyl acetate (50 mL of X3) and the organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure and eluted with silica gel column chromatography eluent system B The resulting residue was purified to give the title product 3-bromo-5-fluorobenzaldehyde 40b (2.57 g, yellow liquid), yield: 81.0percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: at 0 - 20℃; for 2.5 h; Stage #2: at 0 - 20℃; |
Example 13-Difluoromethyl-5-(2,3-difluoro-6-nitrophenoxy)benzonitrile (FIGURE 2;ROUTE A).; step 1 - To a solution of o-propylmagnesium chloride in THF (500 mL of a 2M solution in THF, 1.0 mol) and THF (200 mL) was added a solution of 3,5- dibromofluorobenzene (25; 200 g, 0.79 mol) in THF (100 mL) while maintaining the temperature at ca. 0 C. After rinsing with THF (3 x 20 mL) the mixture was aged for 2 h at ca. 0 0C and then warmed to ca. 20° C and aged for 0.5 h. The reaction was sampled by HPLC and then cooled to ca. 0° C. DMF was added over 0.5 h while maintaining the temperature at ca. 0° C. The mixture was aged 1.5 h at ca. 0° C and then warmed slowly to ca. 20 0C overnight. After sampling by HPLC, the mixture was diluted with heptane (200 mL) and then with a mixture of con HCl (120 mL) diluted to 360 mL with water. Con HCl (50 mL) was added to adjust the pH to < 7. The organic phase was separated, <n="19"/>washed with water (400 mL) and evaporated to dryness to afford 160.8 g (100.5percent) of 28 as a yellow oil which solidified on standing. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: With n-butyllithium In di-isopropyl ether at -78℃; for 0.5 h; Inert atmosphere Stage #2: at -78 - 30℃; for 0.5 h; |
1,3-Dibromo-5-fluoro-benzene (20 g, 78.77 mmol, 1 eq) was dissolved in i-Pr2O (200 mL) in a dried flask under nitrogen. The reaction mixture was cooled to -78 °C and stirred under nitrogen atmosphere. n-BuLi (2.5 M, 31.5 mL, 1 eq) was added drop wise to the above solution and the reaction mixture was stirred at -78 °C for 30 min. After complete addition of n-BuLi, N-methoxy-N-methyl-acetamide (9.75 g, 94.5 mmol, 10.05 mL, 1.2 eq) dropped to the above reaction mixture, while keeping the reaction mixture below -78 °C. After addition, the reaction mixture was warmed slowly to 30 °C for 30 min. The reaction mixture was poured into water (150 mL) and the reaction mixture was stirred for 15 min. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (150 mL), combined organic phase, dried over anhydrous Na2SO4, filtered and evaporated in vacuum to give residue (16 g crude). The residue was purified by flash silica gel chromatography (ISCO®; 120 g CombiFlash® Silica Flash Column, Eluent of 0~10percent Ethyl acetate/Petroleum ether gradient 85 mL/min). Compound was obtained as off-white solid (11.3 g, yield 66percent).1H NMR (400 MHz, CDCl3) δ ppm 7.91 - 7.84 (m, 1H), 7.63 - 7.54 (m, 1H), 7.45 (td, J=2.0, 7.8 Hz, 1H), 2.63 - 2.55 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25 h; Inert atmosphere Stage #2: at 0 - 20℃; for 16 h; |
Synthesis of intermediate I-a: l ,3-dibromo-5-isopropoxy-benzeneTo a solution of NaH 60 percent dispersion in mineral oil (1.89 g, 47.25 mmol) in dry DMF (20 mL) under inert atmosphere was added dropwise at 0°C z'-PrOH (3.62 mL, 47.25 mmol). The mixture was stirred at 0°C for 15 min. Then, a solution of l,3-dibromo-5-fluoro- benzene (1.98 mL, 15.75 mmol) in dry DMF (20 mL) was added dropwise at 0°C. The reaction mixture was stirred for 16 h at room temperature. A saturated solution of NaHC03 was added dropwise and the crude product was extracted with Et20 (2 times), the organic layer was washed with a saturated solution of NaHC03 (3 times), then with a saturated solution of NaCl, dried over MgS04 and concentrated to give I-a as yellow oil in quantitative yield. Ή RMN (300 MHz, CDC13) δ 7.21 (t, J = 1.4 Hz, 1H), 6.97 (d, J = 1.5 Hz, 2H), 4.61-4.40 (m, 1H), 1.32 (d, J= 6.0 Hz, 6H). |