* 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.
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); hydrogen; sodium t-butanolate In methanol at 80℃; for 12 h; Glovebox; Autoclave
General procedure: A glass liner containing a stir bar was charged with substrate (0.5 mmol), base (0.05mmol), Ru-MACHO (5 umol) and MeOH (0.5 mL) in a glove box. The glass linerwas then placed into an autoclave followed by degassing with H2 three times. Thehydrogenation was carried out at 10-50 bar H2 with stirring at 25oC or 80oC for 12-24h. After the reaction finished, the autoclave was allowed to cool down to r.t. Thehydrogen gas was then carefully released in a fume hood, and the solution transferredto a flask with H2O (2 ml), extracted with EA (3x5 ml), dried with Na2SO4 andconcentrated in vacuo to afford the pure product 2a-2s or 3a-3s.
Stage #1: With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone; <i>tert</i>-butyl alcohol at 20℃; for 16 h; Stage #2: With hydrogenchloride In water; acetone; <i>tert</i>-butyl alcohol
4-Bromostyrene (1.0Og, 5.46 mmol) was dissolved in 25 mis of 2: 1 water acetone. To this was added 4-methylmorpholine N-oxide (0.704 g, 6.01 mmole) and osmium tetroxide (0.167 g, 0.061 mmole, 2.5percent in t-BuOH). This mixture was stirred at room temperature for 16 hours, then diluted with EtOAc, washed once with IN aq. HCl, once with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by Flash 40 Biotage ( 4OM cartridge, 100percent EtOAc as the eluant) to give 335 mgs (28percent) of l-(4-bromophenyl)ethane-l,2-diol as a white solid.
Reference：
[1] Organic Letters, 2005, vol. 7, # 22, p. 5071 - 5074
[2] Journal of the American Chemical Society, 2010, vol. 132, # 41, p. 14409 - 14411
[3] Journal of Organic Chemistry, 2015, vol. 79, # 23, p. 11431 - 11439
[4] Tetrahedron Letters, 2007, vol. 48, # 38, p. 6776 - 6778
[5] Chemical Research in Toxicology, 1998, vol. 11, # 1, p. 44 - 53
[6] Journal of Organic Chemistry, 2010, vol. 75, # 7, p. 2321 - 2326
[7] European Journal of Organic Chemistry, 2001, # 10, p. 1937 - 1942
[8] European Journal of Organic Chemistry, 2017, vol. 2017, # 43, p. 6441 - 6444
[9] Journal of the American Chemical Society, 2013, vol. 135, # 3, p. 1148 - 1154
[10] Chemical Communications, 2017, vol. 53, # 94, p. 12634 - 12637
[11] Patent: WO2011/22508, 2011, A2, . Location in patent: Page/Page column 89; 90
[12] Tetrahedron Letters, 2001, vol. 42, # 40, p. 7011 - 7014
[13] Journal of Organic Chemistry, 1996, vol. 61, # 21, p. 7402 - 7407
[14] Patent: WO2006/87169, 2006, A1, . Location in patent: Page/Page column 41
[15] Patent: WO2010/104933, 2010, A1, . Location in patent: Page/Page column 152-153
3
[ 20201-26-7 ]
[ 92093-23-7 ]
Yield
Reaction Conditions
Operation in experiment
81%
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 12 h;
[0160] To a solution of ethyl2-(4-bromophenyl)-2-oxoacetate(LOg, 4.0 mmol) in ethanol (20 mL) was added sodiumborohydride (380 mg, 10.0 mmol) at oo C., and the mixturewas stirred at RT for 12 h. The reaction was quenched withpropan-2-one (1 0 mL) and concentrated under reduced pressure.The resultant was purified by silica gel column chromatography( dichloromethane:methanol= 10: 1) to afford thetitle compound (700 mg, 81percent) as a white solid. MS (ES+)C8H9Br02 requires: 216. found: 217, 219 [M+Ht.
47%
at 0 - 20℃; for 0.166667 h;
To a 50 mL round-bottom flask were added ethyl 4-bromobenzoylformate (0.30 g, 1.2 mmol) and methanol (10 mL), then sodium borohydride (0.13 g, 0.41 mmol) was added in portions at 0°C. The resulting mixture was stirred at rt for 10 min. The reaction mixture was acidified with hydrochloric acid (5.0 mol/L) to pH 6, then the resulting mixture was concentrated in vacuo to remove the methanol. The residue was dissolved in water (50 mL), and the resulting mixture was extracted with ethyl acetate (30 mL*3). The combined organic layers were dried over anhydrous sodium sulfate, concentrated in vacuo, and the residue was purified by silica-gel column chromatography (DCM:MeOH=30:1, V/V) to give a white solid (0.12 g, 47percent). MS(ESI, pos.ion)m/z: 217.9 (M+2);
General procedure: All racemic 1-phenyl-1,2-ethanediols were prepared in quantitative yields by the reduction of the corresponding substituted phenylglyoxal (1 mmol) with NaBH4 (2 mmol) in ethanol (7 mL) at 0 °C to room temperature for 1 h. After completion of the reaction the excess ethanol was removed. The reaction mixture was hydrolysed with dilute HCl and the mixture was extracted with ethyl acetate. The organic layer was dried, concentrated and purified by column chromatography.
With water; 3-chloro-benzenecarboperoxoic acid; at 30℃; for 3h;
10 mL of deionized water was added as a solvent in a round bottom three-necked flask.Weigh 0.190 g (110 mmol/L) of m-CPBA into the flask and shake it to dissolve in deionized water.Thereafter, p-bromostyrene (about 100 mmol/L) was slowly added to the system at a rate of addition of 0.5 mmol/min.The mixture was heated in a water bath at 30 C, and the reaction was vigorously stirred at a rotation speed (300 rpm) for 3 hours.The reaction mixture was extracted with an equal volume of ethyl acetate.The solvent ethyl acetate was evaporated to dryness using a rotary evaporator to give a white solid.
28%
4-Bromostyrene (1.0Og, 5.46 mmol) was dissolved in 25 mis of 2: 1 water acetone. To this was added 4-methylmorpholine N-oxide (0.704 g, 6.01 mmole) and osmium tetroxide (0.167 g, 0.061 mmole, 2.5% in t-BuOH). This mixture was stirred at room temperature for 16 hours, then diluted with EtOAc, washed once with IN aq. HCl, once with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by Flash 40 Biotage ( 4OM cartridge, 100% EtOAc as the eluant) to give 335 mgs (28%) of l-(4-bromophenyl)ethane-l,2-diol as a white solid.
Alternative preparation of chiral 71rans-Lambda/-[2-(4-bromophenyl)cyclopropyl]-2- propanesulfonamide Enantiomer 1 and Enantiomer 2 EPO <DP n="42"/>enantiomer 2enantiomer 1 Intermediate 7 Intermediate 7 enantiomer 2 Enantiomer 1 Enantiomer 2 trans trans; Intermediate 9, Enantiomer 1: chiral 2-(4-bromophenyl)oxirane Enantiomer 1; A 50OmL round bottom flask, equipped with magnetic stirrer, was charged with 10OmL of 1BuOH, 10OmL of water and of AD-mix-beta(30.6g). Stirring at room temperature produced two clear phases; the lower aqueous one appeared bright yellow. The mixture was cooled to 00C whereupon some of the dissolved salts precipitated. 4-Br-styrene (4g, 21.85mmol) was added at once and the heterogeneous slurry was stirred vigorously at 00C for 3h. While the mixture was stirred at 00C, solid sodium sulfite (32.8g) was added and the mixture was allowed to warm to room temperature and stirred for 1h. 20OmL DCM was added to the reaction mixture and after separation of the layers the aqueous one was further extracted with DCM (3x10OmL). Combined organic extracts were dried over Na2SO4 and evaporated to dryness to get 4.9g of crude material as a colourless thick oil.3.9g of this oil (17.97mmol) were dissolved in dry DCM 5OmL, under nitrogen. To this solution trimethylorthacetate (2.962mL, 23.27mmol) was added and the mixture cooled down to O0C. TMS-CI (2.964mL, 23.36mmol) was added dropwise and the reaction mixture left reacting for 1.5h. The volatiles were evaporated and the residue was dissolved in MeOH, treated with K2CO3 (3.1 g) and stirred vigorously at room temperature for 3h. The suspension was filtered, the solid was washed with DCM and the filtrate was evaporated in a rotary evaporator at room temperature under EPO <DP n="43"/>vacuum to get crude title material (3.9g) that was purified by SiO2 flash chromatography eluting with petroleum ether/Et2O from 95/5 to 90/10. Evaporation of the solvent afforded title material, 2.95g, as a colourless oil that became a waxy solid in the fridge. NMR (CDCI3): 7.49 (d,2H), 7.13 (d, 2H), 3.84 (dd, 1 H), 3.13 (dd, 1 H), 2.77 (dd, 1 H). Chiral HPLC: ee 98.6% Analytical Chiral HPLC conditions: column: CHIRALPAK AS-H (25x0.46 cm) mobile phase: n-Hexane/Ethanol 95/5% v/v flow rate: 1 ml/minUV wavelength range: 200-400 nm Rt Enantiomer 1 : 6.1 min 99.3 a/a% Rt Enantiomer 2: 8.5min 0.7 a/a%.
With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; at 20℃; for 1h;
To 4-bromostyrene (Compound [LXI], 366 rag, 2 mmol, 1 eq.) in acetone (10 mL) was added morpholine jV-oxide (953 mg of a 50% solution in H20, 4.0 mmol, 2.0 eq.) and then OsO4 (1.3 g for a 4% OsO4 in H20, 0.2 mmol, 0.1 eq). The mixture was allowed to stir at room temperature for 1 hour. The reaction mixture was then added to an aqueous solution of sodium thiosulfate and then extracted three times with EtOAc. The combined organics were dried over Na2SO4, concentrated, and subjected to silica gel chromatography using EtOAc- heptane as the eluant to provide Compound fLXII]: 1H NMR (400 MHz, METHANOL-d4) delta ppm 3.54 - 3.66 (m, 2 H) 4.66 (dd, /=6.76, 5.10 Hz, 1 H) 7.24 - 7.35 (m, 2 H) 7.41 - 7.53 (m, 2 H).
To a stirring solution of l-(4-bromophenyl)ethane-l,2-diol (3.0 g, 14 mmol), in acetonitrile (25 mL), was added concentrated sulfuric acid (7.4 mL, 0.14 mol). The resulting solution was stirred at room temperature for 1 h, then heated to reflux. After 2 h, the mixture was cooled to room temperature and water (10 mL) was added. The acetonitrile was removed by rotary evaporation. The resulting aqueous slurry was heated to 100 0C. After 2 h, the mixture was cooled to room temperature and DCM was added. The mixture was stirred for 5 min before separating the layers. The organic layer was extracted once more with water, then the combined organic extract was set aside. The aqueous extract was treated with 50% aqueous NaOH to pH 10, then extracted with EtOAc (thrice). The combined EtOAc extracts were washed with brine, dried over sodium sulfate, and then the solvents were evaporated to give the title compound (1.9 g, 64%). Exact mass calculated for CsH10BrNO: 215.0, found: LCMS m/z = 216.3 [M+H]+.
Alternative preparation of chiral 71rans-Lambda/-[2-(4-bromophenyl)cyclopropyl]-2- propanesulfonamide Enantiomer 1 and Enantiomer 2 EPO <DP n="42"/>enantiomer 2enantiomer 1 Intermediate 7 Intermediate 7 enantiomer 2 Enantiomer 1 Enantiomer 2 trans trans; Intermediate 9, Enantiomer 1: chiral 2-(4-bromophenyl)oxirane Enantiomer 1; A 50OmL round bottom flask, equipped with magnetic stirrer, was charged with 10OmL of 1BuOH, 10OmL of water and of AD-mix-beta(30.6g). Stirring at room temperature produced two clear phases; the lower aqueous one appeared bright yellow. The mixture was cooled to 00C whereupon some of the dissolved salts precipitated. 4-Br-styrene (4g, 21.85mmol) was added at once and the heterogeneous slurry was stirred vigorously at 00C for 3h. While the mixture was stirred at 00C, solid sodium sulfite (32.8g) was added and the mixture was allowed to warm to room temperature and stirred for 1h. 20OmL DCM was added to the reaction mixture and after separation of the layers the aqueous one was further extracted with DCM (3x10OmL). Combined organic extracts were dried over Na2SO4 and evaporated to dryness to get 4.9g of crude material as a colourless thick oil.3.9g of this oil (17.97mmol) were dissolved in dry DCM 5OmL, under nitrogen. To this solution trimethylorthacetate (2.962mL, 23.27mmol) was added and the mixture cooled down to O0C. TMS-CI (2.964mL, 23.36mmol) was added dropwise and the reaction mixture left reacting for 1.5h. The volatiles were evaporated and the residue was dissolved in MeOH, treated with K2CO3 (3.1 g) and stirred vigorously at room temperature for 3h. The suspension was filtered, the solid was washed with DCM and the filtrate was evaporated in a rotary evaporator at room temperature under EPO <DP n="43"/>vacuum to get crude title material (3.9g) that was purified by SiO2 flash chromatography eluting with petroleum ether/Et2O from 95/5 to 90/10. Evaporation of the solvent afforded title material, 2.95g, as a colourless oil that became a waxy solid in the fridge. NMR (CDCI3): 7.49 (d,2H), 7.13 (d, 2H), 3.84 (dd, 1 H), 3.13 (dd, 1 H), 2.77 (dd, 1 H). Chiral HPLC: ee 98.6% Analytical Chiral HPLC conditions: column: CHIRALPAK AS-H (25x0.46 cm) mobile phase: n-Hexane/Ethanol 95/5% v/v flow rate: 1 ml/minUV wavelength range: 200-400 nm Rt Enantiomer 1 : 6.1 min 99.3 a/a% Rt Enantiomer 2: 8.5min 0.7 a/a%.
pyridinium p-toluenesulfonate; In acetone; for 16h;
To a mixture of l-(4-bromophenyl)ethane-l,2-diol (1.0 g, 4.6 mmol) in acetone (10 mL) and 2,2-dimethoxypropane (11 mL, 92 mmol) was added pyridiniumj?-toluenesulfonate (PPTs) (0.12 g, 0.46 mmol). After 16 h, the reaction was quenched with water. The volatiles were evaporated and the aqueous slurry was extracted with DCM (thrice). The combined organic phase was washed with brine, dried over sodium sulfate, and then the solvent was evaporated to give the title compound as a yellow oil (1.2 g, 98%). 1H NMR (400 MHz, DMSO-J6) delta ppm 1.39 (s, 3H), 1.45 (s, 3H), 3.55 (dd, J= 8.0, 8.0 Hz, 1 H), 4.30 (dd, J= 8.0, 6.8 Hz, 1 H), 5.05 (dd, J= 6.8, 6.8 Hz, 1 H), 7.33 (d, J = 8.3 Hz, 2H), 7.56 (d, J = 8.3 Hz, 2H).
61%
With toluene-4-sulfonic acid; In acetone; at 20℃;
[0162] To a solution of 1-( 4-bromophenyl)ethane-1 ,2-diol(700 mg, 3.2 mmol) and 2,2-dimethoxypropane (666 mg, 6.4mmol) in propan-2-one (10 mL) was added 4-methylbenzenesulfonicacid (11 0 mg, 0.64 mmol), and the reaction mixturewas stirred at RT overnight. The mixture was concentratedunder reduced pressure. The residue was purified bysilica gel colunm chromatography (ethyl acetate: petroleumether= :10) to afford the title compound (500 mg, 61 %) as alight yellow oiL MS (ES+) C11 H13Br02 requires: 256. found:257, 259 [M+Ht.
l-(4-bromophenyl)ethane-l,2-diol (0.15 g, 0.69 mmol) was dissolved in 7 mis of dry acetonitrile, followed by the addition of carbonyldiimidazole (0.17g, 1.04 mmol). This mixture was warmed to 40 0C for 1.5 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc and washed with saturated ammonium chloride solution, water, dried over sodium sulfate and concentrated under reduced pressure. 1Og Sep Pak purification (1: 1 EtOAc:Hexanes) afforded 0.095 g of 4-(4-bromophenyl)-l,3-dioxolan-2-one (57%) as a white solid.
General procedure: All racemic 1-phenyl-1,2-ethanediols were prepared in quantitative yields by the reduction of the corresponding substituted phenylglyoxal (1 mmol) with NaBH4 (2 mmol) in ethanol (7 mL) at 0 C to room temperature for 1 h. After completion of the reaction the excess ethanol was removed. The reaction mixture was hydrolysed with dilute HCl and the mixture was extracted with ethyl acetate. The organic layer was dried, concentrated and purified by column chromatography.
With tert.-butylhydroperoxide; potassium tert-butylate; In water; at 80℃; for 8h;
General procedure: In a 25mL round-bottom flask, t-BuOK (1.5mmol) was dissolved in water (0.5mL), and diol (0.5mmol) was added. Subsequently, aq 70% TBHP (2mmol) was slowly added to this flask. The resulting suspension was then heated at 80C (using oil bath) for 8h. After completion of reaction this slurry was cooled to room temperature. The slurry was then acidified with 2M hydrochloric acid until the aqueous layer was strongly acidic by pH paper. This on simple filtration resulted in pure carboxylic acids. Note: alternate work-up procedure: The reaction mixture was then cooled to room temperature and then extracted with ethyl acetate (2×10mL) and combined organic phase was washed with saturated brine solution and dried over anhydrous Na2SO4. After removal of the solvent under reduced pressure to afford carboxylic acids.
With pyridinium p-toluenesulfonate; In toluene; at 20 - 40℃; for 18h;
General procedure: A diol 6c or 6d or 6e (2 equiv) and PPTS (0.1 equiv) was added to a toluene (25.0 mL/1 mmol of substrate) solution of a substituted-4,4-dimethoxycyclohexa-2,5-dienone 5a or 5b (1 equiv) at room temperature. After stirring at 40 C for 18 h, the reaction mixture was quenched by the addition of saturated aqueous NaHCO3 and the product was extracted with ethyl acetate three times. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulphate, filtered, and concentrated under reduced pressure. The residue was purified by preparative TLC to give the title compound.
(±)-2-(4-bromophenyl)-7-chloro-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With pyridinium p-toluenesulfonate; In toluene; at 20 - 40℃; for 18h;
General procedure: A diol 6c or 6d or 6e (2 equiv) and PPTS (0.1 equiv) was added to a toluene (25.0 mL/1 mmol of substrate) solution of a substituted-4,4-dimethoxycyclohexa-2,5-dienone 5a or 5b (1 equiv) at room temperature. After stirring at 40 C for 18 h, the reaction mixture was quenched by the addition of saturated aqueous NaHCO3 and the product was extracted with ethyl acetate three times. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulphate, filtered, and concentrated under reduced pressure. The residue was purified by preparative TLC to give the title compound.
With sodium tetrahydroborate; In ethanol; at 0 - 20℃; for 12h;
[0160] To a solution of ethyl2-(4-bromophenyl)-2-oxoacetate(LOg, 4.0 mmol) in ethanol (20 mL) was added sodiumborohydride (380 mg, 10.0 mmol) at oo C., and the mixturewas stirred at RT for 12 h. The reaction was quenched withpropan-2-one (1 0 mL) and concentrated under reduced pressure.The resultant was purified by silica gel column chromatography( dichloromethane:methanol= 10: 1) to afford thetitle compound (700 mg, 81%) as a white solid. MS (ES+)C8H9Br02 requires: 216. found: 217, 219 [M+Ht.
47%
With methanol; sodium tetrahydroborate; at 0 - 20℃; for 0.166667h;
To a 50 mL round-bottom flask were added ethyl 4-bromobenzoylformate (0.30 g, 1.2 mmol) and methanol (10 mL), then sodium borohydride (0.13 g, 0.41 mmol) was added in portions at 0C. The resulting mixture was stirred at rt for 10 min. The reaction mixture was acidified with hydrochloric acid (5.0 mol/L) to pH 6, then the resulting mixture was concentrated in vacuo to remove the methanol. The residue was dissolved in water (50 mL), and the resulting mixture was extracted with ethyl acetate (30 mL*3). The combined organic layers were dried over anhydrous sodium sulfate, concentrated in vacuo, and the residue was purified by silica-gel column chromatography (DCM:MeOH=30:1, V/V) to give a white solid (0.12 g, 47%). MS(ESI, pos.ion)m/z: 217.9 (M+2);
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); hydrogen; sodium t-butanolate; In methanol; at 80℃; under 37503.8 Torr; for 12h;Glovebox; Autoclave;
General procedure: A glass liner containing a stir bar was charged with substrate (0.5 mmol), base (0.05mmol), Ru-MACHO (5 umol) and MeOH (0.5 mL) in a glove box. The glass linerwas then placed into an autoclave followed by degassing with H2 three times. Thehydrogenation was carried out at 10-50 bar H2 with stirring at 25oC or 80oC for 12-24h. After the reaction finished, the autoclave was allowed to cool down to r.t. Thehydrogen gas was then carefully released in a fume hood, and the solution transferredto a flask with H2O (2 ml), extracted with EA (3x5 ml), dried with Na2SO4 andconcentrated in vacuo to afford the pure product 2a-2s or 3a-3s.
(E)-2-fluoro-4-(4-bromophenyl)-4-oxobut-2-enoic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With manganese(IV) oxide; In dichloromethane; at 20℃; for 12h;
A mixture of <strong>[92093-23-7]1-(4-bromophenyl)-1,2-ethanediol</strong> (6.45 g, 29.7 mmol) (compound of formula 6)(50 ml) 2-fluoroethoxymethyltriphenylphosphine (compound of formula 2) (9.41 g, 25.7 mmol) was sequentially added. Manganese dioxide (23. 4g, 270mmol), stirring reaction at room temperature for 12 hours, TLC detection reaction is complete, Filtration, concentration, and column chromatography gave 7.23 g of pure product (81% yield) (compound of formula 7).
N-(1-((1-cyanocyclopropyl)carbamoyl)-4,4-difluorocyclohexyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-2-carboxamide[ No CAS ]
N-(1-((1-cyanocyclopropyl)carbamoyl)-4,4-difluorocyclohexyl)-6-(4-(1,2-dihydroxyethyl)phenyl)benzofuran-2-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In N,N-dimethyl-formamide; at 85℃; for 2h;Inert atmosphere;
To a 50 mL two-neck flask were added N-(1-((1-cyanocyclopropyl)carbamoyl)cyclohexyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-2-carboxamide (62 mg, 0.12 mmol), Pd(dppf)Cl2·CH2Cl2 (8 mg, 0.01 mmol) andDMF (8 mL), then potassium carbonate solution (0.10 mL, 0.20 mmol, 2 mol/L) was added under nitrogen protection.The resulting mixture was stirred at 85C for 2 h. The reaction mixture was cooled to rt and the mixture was quenchedwith water (100 mL). The resulting mixture was extracted with EtOAc (30 mL32). The combined organic layers werewashed with saturated brine (20 mL), dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated in vacuo,and the residue was purified by silica-gel column chromatography (DCM:MeOH=30:1, V/V)to give a white solid (42 mg,79%).MS(ESI, pos.ion)m/z: 524.2 (M+1);1H NMR (400 MHz, DMSO-d6) delta: 8.76 (s, 1H), 8.47 (s, 1H), 7.94 (s, 1H), 7.86 (d, J = 8.2 Hz, 1H), 7.69 (dd, J = 15.3,7.8 Hz, 4H), 7.46 (d, J = 7.6 Hz, 2H), 5.28 (d, J = 4.2 Hz, 1H), 4.74 (t, J = 5.7 Hz, 1H), 4.60 (d, J = 4.9 Hz, 1H), 3.48 (t,J = 5.7 Hz, 3H), 2.22 (s, 2H), 2.07 (d, J = 14.8 Hz, 5H), 1.46 (s, 2H), 1.09 (d, J = 5.6 Hz, 2H), 0.86 (s, 2H).19F NMR (376 MHz, DMSO-d6) delta:-92.53 (s), -93.16 (s), -97.79 (s), -98.41 (s).
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