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[ CAS No. 7073-69-0 ]

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Chemical Structure| 7073-69-0
Chemical Structure| 7073-69-0
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CAS No. :7073-69-0 MDL No. :MFCD00767180
Formula : C9H11BrO Boiling Point : 268.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :215.09 g/mol Pubchem ID :329527
Synonyms :

Safety of [ 7073-69-0 ]

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:

Application In Synthesis of [ 7073-69-0 ]

  • Upstream synthesis route of [ 7073-69-0 ]
  • Downstream synthetic route of [ 7073-69-0 ]

[ 7073-69-0 ] Synthesis Path-Upstream   1~20

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Reference: [1] RSC Advances, 2016, vol. 6, # 25, p. 20588 - 20597
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YieldReaction ConditionsOperation in experiment
71%
Stage #2: With ammonium chloride In diethyl ether at -5℃;
General procedure: A 38percent solution of ammonium chloride, 58 mL, was added at –5 °Cto the product obtained by reaction of 26.50 g (0.14 mol) of ester 4a in 35 mL of anhydrous diethylether with methylmagnesium iodide [prepared from 9.1 g (0.37 mol) of magnesium and 53.3 g (0.37 mol) of freshly distilled methyl iodide in 85 mL of anhydrous diethyl ether]. The ether layer was separated by decanting, and the pasty precipitate was extracted with diethyl ether (3 × 35 mL). The extracts were combined, dried over Na2SO4, and evaporated. Yield 19.40 g (82percent), purity 95percent (GLC), bp 99–100°C (5 mm), d420 =1.1576, nD20 = 1.5420; MRD 46.43, calcd. 46.55;published data [19]: mp 23.7°C, bp 79.2°C (2.2 mm),nD20 = 1.5416. IR spectrum, ν, cm–1: 3460, 1175 (OH),1370, 1385 [C(CH3)2], 690 (C–Cl). 1H NMR spectrum,δ, ppm: 1.64 s (6H, CH3), 2.46 s (1H, OH), 6.9–7.7 m(4H, Harom). Found, percent: C 63.00; H 6.42; Cl 20.71.C9H11ClO. Calculated, percent: C 63.35; H 6.50; Cl 20.78.
Reference: [1] Organic Letters, 2013, vol. 15, # 20, p. 5326 - 5329
[2] Russian Journal of Organic Chemistry, 2016, vol. 52, # 6, p. 806 - 812[3] Zh. Org. Khim., 2016, vol. 52, # 6, p. 806 - 812,7
[4] Transactions of the Faraday Society, 1936, vol. 32, p. 1327,1328 Anm.
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YieldReaction ConditionsOperation in experiment
97.48%
Stage #1: at 2 - 15℃; for 19.5 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water at 0 - 15℃; for 2 h;
A 12-Liter 4-neck flask equipped with a thermocouple, condenser, septum, addition funnel and overhead mechanical stirrer under argon was charged with methyl-2-bromobenzoate (226.5 g, 1.05 mol) and THF (1.6 L, 19.66 mol). The mixture was cooled to a temperature between 2 and 5° C. with stirring and held for 30 min. To the solution was slowly added methyl magnesium bromide in diethyl ether (3M, 1.05 L; 3.15 mol) via the addition funnel at a rate to maintain the reaction temperature below 15° C. An exotherm was observed during the addition, the reaction temperature warmed from 3 to 15° C. The addition of 1.05 L Grignard was complete in 4 h (approximate feed rate was 4.17 mL/min). The reaction mixture appeared to be off-white/yellow slurry. The reaction was allowed to warm to room temperature and stirred overnight (15 h). The reaction was sampled by HPLC/TLC and showed no starting material present. The ice bath was again applied to the reaction flask and a 0.5 M HCI solution (4.5 L; 2.25 mol) was slowly added over a period of 2 h. The temperature increased dramatically from 0 to 15° C. After the quench was complete, the reaction was stirred at room temperature for 30 min. Additional 2 N HCl (500 mL; 1.00 mol) was slowly added to maintain a pH less than 6. MTBE (1 L) was added to help with the phase split. The reaction was stirred at room temperature for 1 to 2 h to dissolve the solid material into the aqueous phase (most likely Mg(OH)2 which is very basic). The pH must be checked and adjusted with additional acid when necessary. The phases were separated and the aqueous layer was washed with an additional 1 L MTBE (2.x.500 mL). The organic phases were combined, washed with NaHCO3 solution (2.x.300 mL), dried over MgSO4, filtered and the filtrate was concentrated under vacuum to yield the title Compound 10d (220.83 g, 97.48percent yield) as a clear yellow oil.
91%
Stage #1: at -5 - 20℃; for 1 h; Inert atmosphere
Stage #2: With hydrogenchloride In water at 0 - 20℃; for 0.5 h;
Scheme 17 XCVIII XCVIIStep 1[00252] To a stirring solution of methyl 2-bromobenzoate (XCIV) (5 g, 0.0233 mol) in THF (30 mL) under argon at 0°C was added dropwise MeMgBr (19.4 mL, 0.058 mol), maintaining the temperature in the range of -5 to 0°C. The reaction mixture was stirred at 0°C for 1 hour and then at room temperature overnight. The mixture was cooled to 0°C and 1M aqueous HCl (35 mL) was added, maintaining the temperature below 5°C, after which it was allowed to reach room temperature and was stirred for 30 minutes. To this mixture EtOAc (35 mL) was added and after stirring for 5 minutes a white precipitate was removed by filtration through a Celite pad. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic fractions were concentrated, washed with brine and dried over MgSC^. Crude XCV was purified by silica gel chromatography using DCM then DCM/MeOH 300/1 to give 2- (2-bromophenyl)propan-2-ol (XCV) as a light yellow oil (4.55 g; 21.2 mmol, 91percent yield). 1H NMR (CDCls) δ ppm 1.75 (s, 6H), 2.85 (brs, 1H), 7.09 (td, J=7Hz, J=2Hz, 1H), 7.29 (td, J=7Hz, J=lHz, 1H), 7.58 (dd, J=7, J=l, 1H), 7.67 (dd J=7, J=2, 1H).
82%
Stage #1: at 0 - 20℃; for 2 h;
Stage #2: With hydrogenchloride In diethyl ether; water at 0℃;
To a solution of methyl 2-bromobenzoate (20.76 g, 96 mmol) in 120 mL of anhydrous ether under Argon at 0° C. was slowly added methylmagnesium bromide (77 mL, 3.26 M) at a rate that the internal temperature of the mixture was below 20° C. A white suspension resulted, and the mixture was stirred at room temperature for 2 h. The mixture was cooled in an ice-water bath. To the reaction mixture was very slowly added hydrochloric acid (400 mL, 0.5 M). The pH of the final mixture was adjusted to less than about 6 with few drops of 2M hydrochloric acid. The layers were separated, and the aqueous layer was extracted twice with ether. The organic layers were combined and dried over magnesium sulfate. The organic fraction was filtered, and the filtrate was concentrated to yield the title compound as a pale yellow liquid, which was distilled under vacuum to afford the title Compound 10d as a colorless liquid (16.9 g, 82percent, b.p. about 65-70° C./0.3 mmHg). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.67 (dd, 1H, J=1.7, 7.9 Hz), 7.58 (dd, 1H, J=1.3, 7.9 Hz), 7.30 (ddd, 1H, J=1.4, 7.4, 7.9 Hz), 7.10 (ddd, 1H, J=1.7, 7.4, 7.8 Hz), 2.77 (br s,1H), 1.76 (s, 6H).
Ca. 303 g at 35 - 40℃; Inert atmosphere Methylmagnesium bromide in toluene/THF (1.4 M, 1.24 L) was charged to a vessel under a nitrogen atmosphere. Methyl 2-bromobenzoate (164 g) was added. The reaction mixture was aged at 35-40 °C and assayed for completion. Ethanol (57.3 mL) was added. The mixture was aged at 45 °C for 1h. A solution of pyridine-4-carboxaldehyde (8.09 g) in toluene (16 mL) was added. The mixture was aged at 45-50 °C. A vessel was charged with water (820 mL) and 37percent hydrochloric acid (186 mL) and cooled to 0 °C. The reaction solution was added into the cold aqueous hydrochloric acid solution. The mixture was aged at 20-25 °C, and the lower aqueous layer cut. The organic layer washed with water and the lower aqueous layer cut. The organic layer was concentrated under reduced pressure at 40-50 °C. DMF (-200 mL) was added and concentration continued to afford -303 g solution of IIA as a slightly cloudy oil. 1NMR (500MHz, CDCl3) δ 7.68 (dd, J= 8.0, 1.5 Hz, IH), 7.59 (dd, J= 8.0, 1.5 Hz, IH), 7.31 (m, IH), 7.11 (m, IH), 2.81 (s, IH), 1.76 (s, 6H) 13C NMR (125MHz, CDCl3) δ 146.0, 135.1, 128.5, 127.5, 127.2, 120.4, 73.5, 29.5.

Reference: [1] Patent: US2007/259936, 2007, A1, . Location in patent: Page/Page column 171-172
[2] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1774 - 1783
[3] Patent: WO2012/109164, 2012, A1, . Location in patent: Page/Page column 62
[4] Journal of Organic Chemistry, 2015, vol. 80, # 8, p. 3891 - 3901
[5] Patent: US2007/259936, 2007, A1, . Location in patent: Page/Page column 167
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3859 - 3874
[7] Journal of Organic Chemistry, 2015, vol. 80, # 6, p. 3012 - 3021
[8] Journal of the American Chemical Society, 1978, vol. 100, # 9, p. 2779 - 2789
[9] Journal of the American Chemical Society, 1992, vol. 114, # 14, p. 5878 - 5879
[10] Organic Letters, 2013, vol. 15, # 10, p. 2454 - 2457
[11] Patent: WO2013/185021, 2013, A2, . Location in patent: Page/Page column 40
[12] Patent: WO2014/81616, 2014, A1, . Location in patent: Page/Page column 20; 21
[13] Patent: WO2016/11231, 2016, A1, . Location in patent: Paragraph 0087
[14] Patent: EP1726590, 2006, A1, . Location in patent: Page/Page column 58
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YieldReaction ConditionsOperation in experiment
69%
Stage #1: at 20℃; for 19 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
To a stirred solution of ethyl 2-bromobenzoate (10 g, 46.5 mmol) in tetrahydrofuran (80 mL) was added dropwise a 3.0 M solution of methylmagnesium chloride in tetrahydrofuran (39 mL, 0.116 mol) at room temperature and the mixture was stirred for 19 h at the same temperature. The reaction mixture was quenched by the addition of 2 N hydrochloric acid aqueous solution, and concentrated to give a colorless residue. The crude material was partitioned between diethyl ether and water, and then the organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (150 g) eluting with hexane/ethyl acetate (15/1) to afford 6.91 g (69percent) of the title compound as a colorless oil: 'H-NMR (CDCl3) 8 7.68-7. 57 (2H, m), 7. 33-7. 25 (1H, m), 7.13-7. 07 (1H, m), 1.75 (6H, s).
Reference: [1] Patent: WO2005/92858, 2005, A2, . Location in patent: Page/Page column 141
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YieldReaction ConditionsOperation in experiment
100%
Stage #1: at 20℃; Cooling with ice
Stage #2: With hydrogenchloride In tetrahydrofuran; 2-methyltetrahydrofuran; water at 0℃;
[0383] A 500 mL round-bottomed-flask equipped with a magnetic stir bar and ice- H2O bath was charged with 82a (18.4g, 85.5 mmol) and anhydrous THF (200 mL). MeMgCl (68 mL, 3.0M in 2-methylTHF) was added dropwise through an additional funnel. The mixture was allowed to warm to rt. gradually and stirred overnight. After cooling back to 0 0C, the white milky suspension was carefully treated with HCl (3M) until the upper layer turned clear with white precipitate at the bottom of the flask (pH = 6). The upper clear solution was decanted into a separatory funnel. The precipitate was rinsed with methyl tert-butyl ether (MTBE) (100 mL) 3 times. Combined MTBE with the clear solution and the mixture was washed with H2O (100 mL) 3 times, brine (100 niL), dried over MgSO4, filtered and concentrated under reduced pressure to give 82b as a light yellow oil (20.2g, 100percent).
Reference: [1] Patent: WO2011/19618, 2011, A1, . Location in patent: Page/Page column 137-138
[2] Journal of Organic Chemistry, 2015, vol. 80, # 8, p. 3891 - 3901
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 7, p. 2048 - 2054
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Reference: [1] Tetrahedron Asymmetry, 2011, vol. 22, # 6, p. 619 - 628
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Reference: [1] Organic Letters, 2012, vol. 14, # 2, p. 628 - 631
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Reference: [1] Organic Letters, 2012, vol. 14, # 2, p. 628 - 631
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Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 18, p. 9247 - 9263
[2] Tetrahedron, 1991, vol. 47, # 415, p. 655 - 664
[3] Justus Liebigs Annalen der Chemie, 1939, vol. 541, p. 283,290
[4] Journal of the American Chemical Society, 1971, vol. 93, p. 6205 - 6216
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1979, p. 829 - 837
[6] Journal of Organic Chemistry, 1976, vol. 41, p. 2628 - 2633
[7] Bulletin of the Chemical Society of Japan, 1999, vol. 72, # 8, p. 1879 - 1885
[8] Tetrahedron Letters, 2010, vol. 51, # 41, p. 5399 - 5401
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Reference: [1] Patent: US3959475, 1976, A,
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Reference: [1] Organic Letters, 2012, vol. 14, # 2, p. 628 - 631
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Reference: [1] Organic Letters, 2012, vol. 14, # 2, p. 628 - 631
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  • [ 7154-66-7 ]
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Reference: [1] Collection of Czechoslovak Chemical Communications, 2009, vol. 74, # 1, p. 85 - 99
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Reference: [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 16, p. 3415 - 3421
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Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 8, p. 3891 - 3901
[2] Journal of Organic Chemistry, 2015, vol. 80, # 8, p. 3891 - 3901
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Reference: [1] RSC Advances, 2016, vol. 6, # 25, p. 20588 - 20597
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  • [ 221352-10-9 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With n-butyllithium In tetrahydrofuran at -78 - -70℃; for 2 h;
Stage #2: With Triisopropyl borate In tetrahydrofuran at 20℃;
To a solution of n-BuLi (166 mL, 2.6 M, 432 mmol) in 200 mL of THF at -78° C. under argon was slowly added a solution of Compound 10d (42.2 g, 196 mmol) in 60 mL of THF at a rate that the internal temperature remained below -70° C. The mixture was stirred at -75° C. for 2 h. To the reaction mixture was then added triisopropylborate (59 mL, 255 mmol) in three portions. The mixture was allowed to warm slowly to room temperature overnight. The mixture was then cooled to 0° C., and was carefully quenched with dilute hydrochloric acid (250 mL, 2N). The mixture was then stirred at room temperature for 1 h. The pH of the mixture was checked and adjusted to acidic using additional 2N HCl if prophetic. The two layers were separated, and the aqueous layer was extracted twice with ether. The organic layers were combined, and dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield a pale yellow oil. The residue was then diluted with ethyl acetate (400 mL) and, washed with 1N sodium hydroxide solution (150 mL.x.3). The basic aqueous layers were combined and acidified with 2N HCl. The clear solution turned cloudy when the acid was added. The mixture was extracted with ether (150 mL.x.3). The organic layers were combined and dried with magnesium sulfate. The solution was filtered, and the filtrate was concentrated under reduced pressure to yield the title Compound 10e as a colorless oil (26.2 g, 82percent) which was used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.00 (s,1H), 7.66 (dm,1H, J=7.3 Hz), 7.45 (dt, 1H, J=1.1, 7.7 Hz), 7.40 (dm, 1H, J=7.6 Hz), 7.31 (dt, 1H, J=1.2, 7.1 Hz), 1.44 (s, 6H).
82.4%
Stage #1: With methylmagnesium bromide In tetrahydrofuran at 0℃; Cooling with ice
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -40℃; Cooling with acetone-dry ice
Stage #3: With Triisopropyl borate In tetrahydrofuran; hexane at 20℃;
82c[0384] A 50 mL round-bottomed-flask equipped with a magnetic stir bar and ice- H2O bath was charged with 82b (860 mg, 4.0 mmol) and anhydrous THF (20 mL). MeMgBr (1.3 mL, 2.0 M in THF) was slowly added via a syringe. The mixture was stirred at 0 0C for 10 minute and the ice bath was replaced with a dry ice-acetone bath at -40 0C. BuLi (1.9 mL, 2.5 M in hexanes) was added dropwise via a syringe. The resulting mixture was stirred at -40 0C for another 2h before B(O-ipr)3 (1.4 mL, 4.8 mmol) was added dropwise. The mixture was allowed to warm up to rt gradually and stirred overnight. After carefully quenched the reaction with H2O (1 mL), HCl (3M, 10 mL) was added and the mixture was stirred at rt for Ih. The mixture was extracted with EtOAc (20 mL) 3 times. Combined extracts was washed with H2O (20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give a clear oil. The oil solidified overnight to give 82c as a pale yellow waxy solid (544mg, 82.4percent).
77%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 2 h; Ice/acetone bath
Stage #2: With triethyl borate In tetrahydrofuran; hexane at -70℃;
A 12-Liter 4-neck round bottom flask equipped with a thermocouple, condenser, addition funnel and overhead mechanical stirrer under dry Argon was charged with anhydrous THF, (3 L) and chilled to -70 to -78° C. via a dry ice/acetone bath. n-Butyl lithium (2.5N in hexanes, 860 mL, 2.15 mol) was slowly added via addition funnel. An exotherm was observed as the temperature rose from -78 to -70° C. To the addition funnel was added a solution of Compound 10d (220 g, 979.97 mmol) in anhydrous THF (1 L). The 2-(2-bromophenyl)propan-2-ol solution was slowly added to the n-BuLi solution. The addition took 90 min in order to maintain a reaction temperature below -70° C. After the addition was complete, the reaction mixture was stirred at -70 to -75° C. for 30 min. The triethylborate (230 mL, 1.35 mol) was quickly added in 3 portions at -70° C. An exotherm was observed, the batch temperature rose from -70 to -64° C. The reaction was stirred at -70° C. and slowly warmed to room temperature over night. After the reaction was cooled to 0-5° C., the reaction was slowly quenched with 2 M HCl (1 L, 2.00 mol) added via the addition funnel while maintaining the batch temperature 0-5° C. The reaction mixture was stirred for 1 h. The aqueous phase pH was 9-10. The pH was then adjusted to acidic (4-5) with 2 M HCl (200 mL). The two phases were separated and the aqueous layer was extracted with MTBE (2.x.500 mL). The combined organic phases were dried with anhydrous magnesium sulfate. The solution was filtered and concentrated to yield a yellow oil. The yellow oil was diluted with MTBE (1.5 L) and washed with 1M NaOH (3.x.500 mL). The product containing basic aqueous phases were combined and acidified with 2 M HCl (800 mL) (the clear solution turns turbid with the addition of acid). After stirring the turbid solution for 15 min (pH=4-5) (Note 1), it was extracted with MTBE (2.x.500 mL). The organic phases were combined and dried over MgSO4. The solution was filtered and the filtrate was concentrated to yield the title Compound 10e as a clear yellow oil (121.78 grams, 77percent yield).
40%
Stage #1: With n-butyllithium In tetrahydrofuran at -75 - -65℃; for 0.5 h; Inert atmosphere
Stage #2: With Trimethyl borate In tetrahydrofuran at 20 - 78℃; for 0.5 h;
Step 2[00253] To a solution of n-BuLi (21.2ml, 0.053 mol) in anhydrous THF (160 mL) at - 78°C under argon was slowly added a solution of 2-(2-bromophenyl)propan-2-ol (XCV) (0.0212 mol, 4.55 g) in anhydrous THF (50 mL) while maintaining the temperature below -65°C. After addition was complete, the reaction mixture was stirred at -75°C for 30 min. To this mixture was added in portions trimethyl borate (0.032mol, 3.3 g), and the reaction mixture was stirred at - 78°C for 30 min and then at room temperature overnight. The mixture was cooled to 0°C, carefully quenched with 1M aqueous HCl, and stirred at room temperature for 15 min. The mixture was acidified to pH 3 with 2M HCl and stirring was continued for 1 hour. The two phases were separated and the aqueous layer was extracted with EtOAc. The combined organic phases were dried over MgS04. The crude product was purified by silica gel chromatography using DCM followed by DCM/MeOH 300/1 to give 3,3-dimethylbenzo[c][l,2]oxaborol-l(3H)- ol (XCVI) as a light yellow oil (1.37 g; 8.5 mmol, 40percent yield). 1H NMR (CDC13) δ ppm 1.54 (s, 6H), 7.25-7.29 (m, 1H), 7.33 (d, J=7Hz, 1H), 7.45 (td, J=7Hz, J=lHz, 1H), 7.68 (d, J=7Hz, 1H).

Reference: [1] Patent: US2007/259936, 2007, A1, . Location in patent: Page/Page column 168
[2] Patent: WO2011/19618, 2011, A1, . Location in patent: Page/Page column 137-138
[3] Patent: US2007/259936, 2007, A1, . Location in patent: Page/Page column 172
[4] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1774 - 1783
[5] Patent: WO2012/109164, 2012, A1, . Location in patent: Page/Page column 62-63
[6] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 7, p. 2048 - 2054
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YieldReaction ConditionsOperation in experiment
40%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2 h;
Stage #2: at -78 - 20℃; for 12 h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃; for 1 h;
C.
3,3-dimethyl-3H-benzo[c][1,2]oxaborol-1-ol
To a solution of 2-(2-bromo-phenyl)-propan-2-ol (4.0 g, 18.6 mmol, prepared as described in Egan, W. et al. J. Am. Chem. Soc., 1971, 93, 6205) in 60 mL of anhydrous THF under argon at -78° C. was slowly added n-butyl lithium (15 mL, 2.5 M).
The mixture was stirred at -78° C. for 2 h, and then triisopropylborate (5.5 mL, 24.2 mmol) was added to the mixture.
The mixture was allowed to warm to room temperature and stirred at room temperature for 12 h.
The mixture was then cooled to 0° C. and hydrochloric acid (10 mL, 1N) was added to the mixture until pH was <5.
The mixture was then stirred at room temperature for 1 h.
The two layers were separated.
The aqueous layer was extracted twice with ethyl acetate.
The organic layers were combined, dried with anhydrous sodium sulfate and filtered.
The filtrate was concentrated under reduced pressure to afford a yellow oil.
The oil was purified by chromatography (silica, EtOAc: hexanes,1:3) to afford a white solid (1.16 g, 40percent).
1H NMR (400 MHz, CDCl3) δ (ppm): 7.53 (m, 1H), 7.36 (m, 2H), 7.28 (m, 1H), 1.62 (s, 3H), 1.61 (s, 3H).
Reference: [1] Patent: US2008/146637, 2008, A1, . Location in patent: Page/Page column 44
[2] Tetrahedron Letters, 1999, vol. 40, # 37, p. 6705 - 6708
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YieldReaction ConditionsOperation in experiment
42% With chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II); potassium acetate; XPhos In ethanol at 80℃; for 0.75 h; Inert atmosphere General procedure: A glass vial equipped with a magnetic stir bar and fitted with a Teflon screw cap was charged with BBA (90 mg, 1.0 mmol), KOAc (98 mg, 1.0 mmol) and the aryl halide (0.50 mmol). To this vessel was added EtOH (2.5 mL) and the reaction media was degassed with Argon for 5 minutes. XPhos Pd G2 (79 mg, 10 molpercent) was then added, and the solution was stirred (750 rpm) and heated at 80°C until full conversion was observed. The reaction media was filtered over celite and the crude filtrate was purified using Teledyne Isco Combiflash device (silica gel column chromatography 15 μm) and Hept:DCM (90:10 to 0:100) as solvent.
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 14, p. 2757 - 2761
[2] Tetrahedron Letters, 2017, vol. 58, # 39, p. 3757 - 3759
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Reference: [1] Bulletin of the Chemical Society of Japan, 1999, vol. 72, # 8, p. 1879 - 1885
Historical Records

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[ 7073-69-0 ]

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Aryls

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