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Product Details of [ 23145-07-5 ]

CAS No. :23145-07-5 MDL No. :MFCD03407317
Formula : C8H5BrO Boiling Point : -
Linear Structure Formula :- InChI Key :AYOVPQORFBWFNO-UHFFFAOYSA-N
M.W :197.03 Pubchem ID :90015
Synonyms :

Calculated chemistry of [ 23145-07-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.91
TPSA : 13.14 Ų

Pharmacokinetics

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) : -5.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 3.02
Log Po/w (WLOGP) : 3.2
Log Po/w (MLOGP) : 2.31
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.78

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.63
Solubility : 0.0462 mg/ml ; 0.000234 mol/l
Class : Soluble
Log S (Ali) : -2.96
Solubility : 0.216 mg/ml ; 0.00109 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.14
Solubility : 0.0142 mg/ml ; 0.0000719 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.41

Safety of [ 23145-07-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 23145-07-5 ]

* 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.

  • Upstream synthesis route of [ 23145-07-5 ]
  • Downstream synthetic route of [ 23145-07-5 ]

[ 23145-07-5 ] Synthesis Path-Upstream   1~34

  • 1
  • [ 23145-07-5 ]
  • [ 58546-89-7 ]
Reference: [1] Organometallics, 2018, vol. 37, # 18, p. 2941 - 2944
[2] Organic Letters, 2017, vol. 19, # 11, p. 2809 - 2812
  • 2
  • [ 112598-18-2 ]
  • [ 23145-07-5 ]
YieldReaction ConditionsOperation in experiment
85% With PPA In benzene for 4 h; Heating / reflux To a solution of the product from Step A (8.4g) in benzene (50ML) was added POLYPHOSPHORIC acid (10G). The mixture was heated at reflux for 4 hrs. The reaction was cooled to 0°C and poured into ice water (80ML) and extracted with ether. The ether layer was washed with saturated sodium bicarbonate and brine, dried with MGS04, filtered and concentrated in vacuo to give 4.9g of crude product (85percent).
85% With PPA In benzene for 4 h; Heating / reflux To a solution ol the product from Step A (8.4 g) in benzene (50 ml) was added polyphosphoric acid (10 g). The mixture was heated at reflux lor 4 hrs. The reaction was cooled to 0 C. and poured into ice water (80 ml) and extracted with ether. The ether layer was washed with saturated sodium bicarbonate and brine, dried with MgSO4, filtered and concentrated in vacuo to give 4.9 g ol crude product (85percent)
85%
Stage #1: With phosphoric acid In benzene at 0℃; for 4 h; Heating / reflux
To a solution of the product from Step A (8.4 g) in benzene (50 ml) was added polyphosphoric acid (10 g). The mixture was heated at reflux for 4 hrs. The reaction was cooled to 0 C. and poured into ice water (80 ml) and extracted with ether. The ether layer was washed with saturated sodium bicarbonate and brine, dried with MgSO4, filtered and concentrated in vacuo to give 4.9 g of crude product (85percent)
85% With PPA In benzene for 4 h; Heating / reflux Step B; To a solution of the product from Step A (8.4g) in benzene (50ml) was added polyphosphoric acid (10g). The mixture was heated at reflux for 4 hrs. The reaction was cooled to 0°C and poured into ice water (80ml) and extracted with ether. The ether layer was washed with saturated sodium bicarbonate and brine, dried with MgS04, filtered and concentrated in vacuo to give 4.9g of crude product (85percent)
85% With PPA In benzene for 4 h; Heating / reflux To a solution of the product from Step A (8.4g) in benzene (50mut) was added polyphosphoric acid (10g). The mixture was heated at reflux for 4 hrs. The reaction was cooled to 0°C and poured into ice water (80ml) and extracted with ether. The ether layer was washed with saturated sodium bicarbonate and brine, dried with MgS04, filtered and concentrated in vacuo to give 4.9g of crude product (85percent)
77% for 3 h; Reflux General procedure: A 25 mL round-bottomed flask was charged with 2-aryloxyacetaldehyde diethyl acetals (1 mmol), Sn-b (0.1 g), andtrifluorotoluene (10 mL). The mixture was stirred under refluxingcondition and monitored by GC. Upon completion, the mixture wascooled to room temperature, and the catalyst Sn-b was filtrate off.The filter cake was washed with trifluorotoluene (10 mL3). Thecombined filtratewas concentrated under vacuum. The residuewaspurified by flash column chromatography on SiO2 (petroleumether/ethyl acetate) to afford the desired 2,3-unsubstituted benzo[b]furans.
59% With polyphosphoric acid In toluene for 3 h; Reflux Step 2.
5-Bromobenzofuran
A solution of 1-bromo-4-(2,2-diethoxyethoxy)benzene (5 g, 17.29 mmol, 1.00 equiv), polyphosphoric acid (13 g, 132.65 mmol, 8.00 equiv) and toluene (50 mL) was heated to reflux for 3 hr in an oil bath.
The resulting mixture was concentrated under vacuum, diluted with 50 mL of ethyl acetate, and washed with 3*50 mL of water and 2*50 mL of saturated sodium bicarbonate.
The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum.
The residue was applied onto a silica gel column (ethyl acetate/petroleum ether (1:10)).
This resulted in 2 g (59percent) of 5-bromobenzofuran as a yellow oil.
1H-NMR (300 MHz, CDCl3, ppm): 7.759-7.751 (d, J=2.4 Hz, 1H), 7.649-7.642 (d, J=2.1 Hz, 1H), 7.442-7.381 (s, 2H), 6.748-6.741 (s, 1H)
50% With PPA In chlorobenzene for 16 h; Heating / reflux Phosphoric acid (40 g) was added to a solution of l-bromo-4-(2,2-diethoxyethoxy)benzene (51.9 mmol) in chlorobenzene (80 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was allowed to cool to rt and the chlorobenzene layer was decanted. The residue was washed with toluene (2 x 30 mL) and the combined organic layers were concentrated. The residue was purified by Flash chromatography (hexane) to provide 5-bromobenzofuran in 50percent yield as colorless oil.
50% With phosphoric acid In chlorobenzene for 16 h; Reflux 2. Synthesis of 5-bromobenzofuran.Phosphoric acid (40 g) was added to a solution of l-bromo-4-(2,2- diethoxyethoxy)benzene (51.9 mmol) in chlorobenzene (80 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was allowed to cool to rt and the chlorobenzene layer was decanted. The residue was washed with toluene (2 x 30 mL) and the combined organic layers were concentrated. The residue was purified by Flash chromatography (hexane) to provide 5-bromobenzofuran in 50percent yield as colorless oil.
50% With phosphoric acid In chlorobenzene for 16 h; Reflux 2. Synthesis of 5-bromobenzofuran.Phosphoric acid (40 g) was added to a solution of l-bromo-4-(2,2- diethoxyethoxy)benzene (51.9 mmol) in chlorobenzene (80 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was allowed to cool to rt and the chlorobenzene layer was decanted. The residue was washed with toluene (2 x 30 mL) and the combined organic layers were concentrated. The residue was purified by Flash chromatography (hexane) to provide 5-bromobenzofuran in 50percent yield as colorless oil.

Reference: [1] Patent: WO2004/33440, 2004, A1, . Location in patent: Page 239-240
[2] Patent: US2004/147559, 2004, A1, . Location in patent: Page 122
[3] Patent: US2004/106794, 2004, A1, . Location in patent: Page 123
[4] Patent: WO2005/66147, 2005, A1, . Location in patent: Page/Page column 209
[5] Patent: WO2005/68460, 2005, A1, . Location in patent: Page/Page column 203
[6] Tetrahedron, 2015, vol. 71, # 29, p. 4835 - 4841
[7] Patent: US2012/277224, 2012, A1, . Location in patent: Page/Page column 15-16
[8] Patent: WO2009/23844, 2009, A2, . Location in patent: Page/Page column 133
[9] Patent: WO2010/21797, 2010, A1, . Location in patent: Page/Page column 98
[10] Patent: WO2010/24980, 2010, A1, . Location in patent: Page/Page column 116
[11] Journal of Medicinal Chemistry, 1997, vol. 40, # 3, p. 322 - 330
[12] Heterocyclic Communications, 2010, vol. 16, # 4-6, p. 249 - 252
[13] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6564 - 6567
[14] European Journal of Organic Chemistry, 2018, vol. 2018, # 22, p. 2774 - 2779
  • 3
  • [ 129969-69-3 ]
  • [ 23145-07-5 ]
YieldReaction ConditionsOperation in experiment
25%
Stage #1: With phosphoric acid In water at 100℃;
Stage #2: With sodium carbonate In water
A mixture of l-bromo-4-(2,2-dimethoxyethoxy)benzene (200 mmol) and polyphosphoric acid (30 mL) was heated to 100 °C and stirred overnight. The reaction mixture was cooled to room temperature and poured into aqueous sodium carbonate until the pH was ~7 to 8. Then the mixture was extracted with dichloromethane (4 x 100 mL) and the organic layers were combined, washed with water (100 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The mixture was distilled under reduced pressure (95 °C, 5 mm Hg) to give a clear oil as the title product (25percent). .H NMR (300 MHz, DMSO-i 6): δ 8.04 (s, 1 H), 7.87 (s, 1 H), 7.59 (d, J= 8.4 Hz, 1 H), 7.44 (d, J= 8.4 Hz, 1 H), 6.95 (s, 1 H).
179 g for 28 h; Reflux Chlorobenzene (1200 mL) was added to a 5000 mL three-necked bottomed flask and the crude crude 1-bromo-4 '- (2,2-dimethoxyethyl) benzene (350 g) (870 g).Stirring was started and heated to reflux for 28 hours.TLC and GC tracking reactions.After completion of the reaction, the reaction solution was cooled to room temperature and the lower layer was separated.The organic phase was washed with water (600 mL) and sodium hydroxide (2 mol / L, 600 mL).Dried over sodium sulfate overnight.Distillation to remove most of the chlorobenzene.The crude product 5-bromobenzofuran (245 g) was then distilled under reduced pressure.After the distillation of pure 5-bromobenzofuran 179 g, the yield of 74.9percent.
Reference: [1] Patent: WO2011/66211, 2011, A1, . Location in patent: Page/Page column 52
[2] Journal of Materials Chemistry, 2001, vol. 11, # 11, p. 2759 - 2772
[3] Patent: CN103724304, 2016, B, . Location in patent: Paragraph 0022; 0024
  • 4
  • [ 24589-89-7 ]
  • [ 108-24-7 ]
  • [ 23145-07-5 ]
YieldReaction ConditionsOperation in experiment
40% at 100℃; for 20 h; Heating / reflux To a mixture of 2-formyl-4-bromophenoxy acetic acid [(50G,] 0. [192MOL),] sodium acetate [(100G,] 1. 21mol) in acetic acid (250mL) at [100°C] was added acetic anhydride [(LOOML)] portions during a period of 3h. The reaction mixture was then refluxed for 20h. The solvent was removed by distillation and residue diluted with 3N HCl [(500ML)] and refluxed for 2h. The reaction mixture was then concentrated under vacuum and product extracted with pet. ether [(3X200ML).] The organic layer was washed with 10percent [NAHC03] solution and evaporated to give [5-BROMO-1-BENZOFURAN] [(15G,] 40percent) as a pale yellow liquid.
Reference: [1] Patent: WO2004/7491, 2004, A1, . Location in patent: Page 51-52
  • 5
  • [ 204452-94-8 ]
  • [ 23145-07-5 ]
  • [ 128868-60-0 ]
Reference: [1] Patent: US2018/170909, 2018, A1, . Location in patent: Paragraph 0818; 0819
  • 6
  • [ 66826-78-6 ]
  • [ 23145-07-5 ]
Reference: [1] Heterocycles, 1997, vol. 45, # 9, p. 1657 - 1661
  • 7
  • [ 7252-83-7 ]
  • [ 106-41-2 ]
  • [ 23145-07-5 ]
Reference: [1] Patent: US5700809, 1997, A,
  • 8
  • [ 863659-59-0 ]
  • [ 23145-07-5 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 32, p. 7746 - 7755
  • 9
  • [ 96853-37-1 ]
  • [ 23145-07-5 ]
Reference: [1] Synlett, 2006, # 4, p. 567 - 570
  • 10
  • [ 106-41-2 ]
  • [ 23145-07-5 ]
Reference: [1] Heterocyclic Communications, 2010, vol. 16, # 4-6, p. 249 - 252
[2] Patent: US2012/277224, 2012, A1,
[3] Patent: WO2011/66211, 2011, A1,
[4] Tetrahedron, 2015, vol. 71, # 29, p. 4835 - 4841
[5] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6564 - 6567
[6] Patent: CN103724304, 2016, B,
[7] European Journal of Organic Chemistry, 2018, vol. 2018, # 22, p. 2774 - 2779
  • 11
  • [ 271-89-6 ]
  • [ 23145-07-5 ]
  • [ 23145-08-6 ]
Reference: [1] Heterocycles, 2001, vol. 54, # 2, p. 825 - 831
  • 12
  • [ 106-41-2 ]
  • [ 23145-07-5 ]
  • [ 128868-60-0 ]
Reference: [1] Patent: EP1204654, 2003, B1,
[2] Patent: EP1204654, , A1, [2] Patent: , 2002, ,
  • 13
  • [ 61131-72-4 ]
  • [ 23145-07-5 ]
Reference: [1] Synlett, 2006, # 4, p. 567 - 570
  • 14
  • [ 1761-61-1 ]
  • [ 23145-07-5 ]
Reference: [1] Synlett, 2006, # 4, p. 567 - 570
  • 15
  • [ 104743-20-6 ]
  • [ 23145-07-5 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 32, p. 7746 - 7755
  • 16
  • [ 13997-74-5 ]
  • [ 23145-07-5 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 32, p. 7746 - 7755
  • 17
  • [ 79-11-8 ]
  • [ 1761-61-1 ]
  • [ 23145-07-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1900, vol. 312, p. 332
  • 18
  • [ 591-20-8 ]
  • [ 23145-07-5 ]
  • [ 128868-60-0 ]
Reference: [1] Patent: US2018/170909, 2018, A1,
  • 19
  • [ 23145-07-5 ]
  • [ 90721-27-0 ]
Reference: [1] Patent: WO2017/155909, 2017, A1,
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
  • 20
  • [ 23145-07-5 ]
  • [ 68-12-2 ]
  • [ 10035-16-2 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2 h;
Stage #2: for 1 h;
Weigh (950 mg, 4.82 mmol)Soluble12 mL anhydrous ether and cooled to -78 ° C. 1.3 M tert-butyllithium in pentane (7.85 mL, 10.2 mmol) was added dropwise to the supernatant. The reaction was stirred at -78 ° C for 2 hours,DMF (0.8 mL, 10.3 mmol) and diethyl ether (1 mL). After 1 h reaction, quench with ammonium chloride at -78 ° C. Ethyl acetate extraction, anhydrous sulfur Sodium sulfate dried, concentrated, and passed through a silica gel column to give a yield of 75percent.
70% With tert.-butyl lithium In diethyl ether; pentane at -78 - 8℃; for 0.833333 h; A solution of 5-bromobenzofuran (950 mg, 4.82 [MMOL)] in anhydrous ether (12 mL) was cooled to-78 [°C.] 1.7 M [TELT-BULI] solution in pentane (6 [ML,] 10.2 [MMOL)] was added dropwise under argon. After addition, the mixture was stirred at-78 °C for 20 min, followed by addition of a mixture of DMF (0.8 mL) and ether (1 mL). The mixture was allowed to warm to rt and stirred for 0.5 h. Ethyl acetate was added. The mixture was poured to saturated ammonium chloride solution. The organic layer was separated and concentrated. The residue was purified by column chromatography (ethyl acetate-hexanes, 1: 5 [V/V)] to give the title compound as a pale yellow solid (490 mg, [70percent).]
70%
Stage #1: With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 0.333333 h;
Stage #2: at -78 - 20℃; for 0.5 h;
A solution of 5-bromobenzofuran (950 mg, 4.82 mmol) in anhydrous ether (12 mL) was cooled to-78 °C. 1.7 M tert-BuLi solution in pentane (6 ml, 10.2 mmol) was added dropwise under argon. After addition, the mixture was stirred at-78 °C for 20 min, followed by addition of a mixture of DMF (0.8 mL) and ether (1 mL). The mixture was allowed to warm to rt and stirred for 0.5 h. Ethyl acetate was added. The mixture was poured to saturated ammonium chloride solution. The organic layer was separated and concentrated. The residue was purified by column chromatography (ethyl acetate-hexanes, 1: 5 v/v) to give the title compound as a pale yellow solid (490 mg, 70percent).
67% With ammonium chloride; tert.-butyl lithium In benzene at -25 - 20℃; for 3 h; To a solution of the product from Step B (2 g) in ether (20 ml) at -78 C. was added t-BuLi dropwise. After stirring for 20 min, DMF (950 mg) was added dropwise and the mixture was stirred at ?25 C. for 3 hrs and then warmed to room temperature overnight. Saturated ammonium chloride was added and the solution was extracted with ether. The ether layer was washed with brine, dried with MgSO4, filtered and concentrated in vacuo to give 980 mg of crude product (67percent).
67%
Stage #1: With tert.-butyl lithium In diethyl ether at -78℃; for 0.333333 h;
Stage #2: at -25 - 20℃;
Step C; To a solution of the product from Step B (2g) in ether (20mut) at-78°C was added t-BuLi dropwise. After stirring for 20min, DMF (950mg) was added dropwise and the mixture was stirred at-25°C for 3hrs and then warmed to room temperature overnight. Saturated ammonium chloride was added and the solution was extracted with ether. The ether layer was washed with brine, dried with MgS04, filtered and concentrated in vacuo to give 980mg of crude product (67percent).
67%
Stage #1: With tert.-butyl lithium In diethyl ether at -78℃; for 0.333333 h;
Stage #2: at -25 - 20℃;
To a solution of the product from Step B (2g) in ether (20ml) at-78°C was added t-BuLi dropwise. After stirring for 20min, DMF (950mg) was added dropwise and the mixture was stirred at-25°C for 3hrs and then warmed to room temperature overnight. Saturated ammonium chloride was added and the solution was extracted with ether. The ether layer was washed with brine, dried with MgS04, filtered and concentrated in vacuo to give 980mg of crude product (67percent).
54%
Stage #1: With iodine In tetrahydrofuran for 2.5 h; Heating / reflux
Stage #2: at -40 - 20℃; for 12 h;
A mixture [OF 5-BROMO-1-BENZOFURAN (0. 5G),] Mg (0.92g, 0. [038MOL), I2] (1 crystal) in dry THF (2. [5ML)] under N2 atmosphere was refluxed for 30min. To this was added a solution of 5- [BROMO-1-BENZOFURAN] (4. [5G)] in 25mL of dry THF) as soon as [THE I2 COLOR] disappear and refluxed for another 2h. The reaction mixture was then cooled to-40°C and added dry DMF (3.6g) drop-wise and slowly warmed to RT for a period of 12h. The reaction mixture was then cooled to 0°C and acidified with 3N HCl to pH=2 and stirred for 30min. The reaction mixture was then diluted with water [(500ML),] extracted with ethylacetate [(2X200ML),] washed with brine and dried. The solvent was removed under vacuum and purified by column chromatography over silica gel (pet. [ETHER/CH2CL2)] to give 5-formyl-1- [BENZOFURAN] (2g, 54percent) as a liquid. LC-MS: M/Z ESI: 1.47 min, [14734 (M+1).]

Reference: [1] Patent: CN107266413, 2017, A, . Location in patent: Paragraph 0188; 0190; 0191; 0192
[2] Patent: WO2004/11418, 2004, A1, . Location in patent: Page 161
[3] Patent: WO2005/68460, 2005, A1, . Location in patent: Page/Page column 318
[4] Patent: US2004/106794, 2004, A1, . Location in patent: Page 123
[5] Patent: WO2005/66147, 2005, A1, . Location in patent: Page/Page column 209
[6] Patent: WO2005/68460, 2005, A1, . Location in patent: Page/Page column 203
[7] Patent: WO2004/7491, 2004, A1, . Location in patent: Page 52
[8] Journal of Medicinal Chemistry, 1997, vol. 40, # 3, p. 322 - 330
  • 21
  • [ 23145-07-5 ]
  • [ 10035-16-2 ]
Reference: [1] Patent: US5229381, 1993, A,
[2] Patent: EP125059, 1991, B1,
  • 22
  • [ 23145-07-5 ]
  • [ 106-41-2 ]
  • [ 2032-35-1 ]
  • [ 10035-16-2 ]
Reference: [1] Patent: US4664693, 1987, A,
  • 23
  • [ 23145-07-5 ]
  • [ 79002-39-4 ]
YieldReaction ConditionsOperation in experiment
85% for 12 h; Inert atmosphere; Reflux General procedure: A mixture of 15, 9k or 9m (190 mmol) and CuCN (49.00 g, 570 mmol) in DMF (500 mL) werestirred at 130 °C (for 15 and 9m) or reflux (for 9k) in N2 atmosphere for 12 h, when TLC analysisindicated completion of reaction. On cooling to room temperature, the reaction mixture was dilutedwith CH2Cl2 (1000 mL), and the resulting mixture was further stirred for 1 h and filtered off. Thefiltrate was washed with 5percent brine (500 mL × 5), dried (Na2SO4) and evaporated on a rotaryevaporator, which was purified by column chromatography to afford 16, 10k or 10m.
Reference: [1] Molecules, 2018, vol. 23, # 2,
[2] Patent: US4341792, 1982, A,
[3] Patent: WO2015/89842, 2015, A1, . Location in patent: Page/Page column 92
[4] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 75 - 83
  • 24
  • [ 23145-07-5 ]
  • [ 79002-39-4 ]
Reference: [1] Patent: WO2015/95261, 2015, A1, . Location in patent: Page/Page column 93
  • 25
  • [ 23145-07-5 ]
  • [ 79002-39-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2541 - 2545
  • 26
  • [ 23145-07-5 ]
  • [ 544-92-3 ]
  • [ 79002-39-4 ]
Reference: [1] Journal of Materials Chemistry, 2001, vol. 11, # 11, p. 2759 - 2772
  • 27
  • [ 23145-07-5 ]
  • [ 331834-13-0 ]
Reference: [1] Patent: EP1481965, 2004, A1, . Location in patent: Page 23
[2] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
  • 28
  • [ 23145-07-5 ]
  • [ 121-43-7 ]
  • [ 331834-13-0 ]
YieldReaction ConditionsOperation in experiment
551 mg
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -60℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; for 4 h; Inert atmosphere
(Preparation 7)
A solution of n-butyl lithium in hexane (1.5M; 3.72 ml, 5.6 mmol) was added dropwise to a solution of 5-bromobenzo[b]furan (1.0 g, 5.0 mmol) in tetrahydrofuran (10 ml) under argon atmosphere at -60° C. and the mixture was stirred at the same temperature for 30 min.
To the mixture was added trimethyl borate (0.69 ml, 6.0 mmol) and temperature of the mixture was raised to room temperature in 4 hrs.
Water (5 ml) was added to the reaction mixture at 5° C. and tetrahydrofuran was distilled off under reduced pressure.
To the residue was added 1N hydrochloric acid (pH 1) and the mixture was extracted with ethyl acetate.
The organic layer was washed with brine and dried.
The solvent was distilled off and the residue was triturated with a mixture of n-hexane/diethyl ether, filtered and dried to give 5-benzo[b]furan boronic acid (551 mg) as a pale brown solid.
Reference: [1] Patent: EP2959918, 2015, A1, . Location in patent: Paragraph 0089
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  • [ 5419-55-6 ]
  • [ 7732-18-5 ]
  • [ 331834-13-0 ]
Reference: [1] Patent: WO2012/119046, 2012, A2, . Location in patent: Page/Page column 89
  • 30
  • [ 23145-07-5 ]
  • [ 13675-18-8 ]
  • [ 331834-13-0 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
  • 31
  • [ 23145-07-5 ]
  • [ 331833-99-9 ]
Reference: [1] Journal of Materials Chemistry, 2001, vol. 11, # 11, p. 2759 - 2772
[2] Patent: WO2010/111483, 2010, A1, . Location in patent: Page/Page column 158
  • 32
  • [ 23145-07-5 ]
  • [ 331833-83-1 ]
Reference: [1] Journal of Materials Chemistry, 2001, vol. 11, # 11, p. 2759 - 2772
[2] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 75 - 83
  • 33
  • [ 23145-07-5 ]
  • [ 869885-60-9 ]
YieldReaction ConditionsOperation in experiment
15%
Stage #1: With 2-iodo-propane; iodine; magnesium In tetrahydrofuran for 1 h; Heating / reflux
Stage #2: With sulfuryl dichloride In tetrahydrofuran at -40 - -30℃; for 0.833333 h;
Isopropyl iodide (15.0 mmol) was added dropwise to a suspension of iodine (0.12 mmol), magnesium (30.0 mmol) in tetrahydrofuran (25 mL). After 15 min, a solution of 5-bromobenzofuran (15.2 mmol) in tetrahydrofuran (25 mL) was added dropwise and the reaction mixture was heated at reflux for 1 h. The mixture was cooled to -30 °C and sulfonyl chloride was bubbled through the reaction mixture for 10 min. The mixture was maintained for 30 min whereupon sulfuryl chloride (15.1 mmol) was added dropwise while cooling to -30 to -40 °C. The resulting solution was maintained for an <n="135"/>additional 10 min and was allowed to warm to rt. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was diluted with dichloromethane (150 mL), washed with brine (3 x 100 mL), dried (sodium sulfate), and concentrated. The residue was purified by Flash chromatography (100/1 to 50/1 petroleum ether/ethyl acetate) to provide benzofuran-5-sulfonyl chloride in 15percent yield as a white solid. Data: 1H NMR (CDCl3) δ 8.37 (s, 1H), 8.00 (d, 1H), 7.84 (s, 1H), 7.44 (d, 1H), 6.97 (s, 1H). LC/MS (ES) m/z 286 [M+BnH-l]+.
15%
Stage #1: With 2-iodo-propane; magnesium In tetrahydrofuranReflux
Stage #2: With sulfur dioxide In tetrahydrofuran at -30℃; for 0.666667 h;
Stage #3: With sulfuryl dichloride In tetrahydrofuran at -40 - 20℃;
3. Synthesis of benzofuran-5-sulfonyl chloride.Isopropyl iodide (15.0 mmol) was added dropwise to a suspension of iodine (0.12 mmol), magnesium (30.0 mmol) in tetrahydrofuran (25 mL). After 15 min, a solution of 5- bromobenzofuran (15.2 mmol) in tetrahydrofuran (25 mL) was added dropwise and the reaction mixture was heated at reflux for 1 h. The mixture was cooled to -30 0C and sulfonyl chloride was bubbled through the reaction mixture for 10 min. The mixture was maintained for 30 min whereupon sulfuryl chloride (15.1 mmol) was added dropwise while cooling to -30 to -40 0C. The resulting solution was maintained for an additional 10 min and was allowed to warm to it. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was diluted with dichloromethane (150 mL), washed with brine (3 x 100 mL), dried (sodium sulfate), and concentrated. The residue was purified by Flash chromatography (100/1 to 50/1 petroleum ether/ethyl acetate) to provide benzofuran-5-sulfonyl chloride in 15percent yield as a white solid. Data: 1H NMR (CDCl3) δ 8.37 (s, IH), 8.00 (d, IH), 7.84 (s, IH), 7.44 (d, IH), 6.97 (s, IH). LC/MS (ES) m/z 286 [M+BnH-l]+.
15%
Stage #1: With 2-iodo-propane; iodine; magnesium In tetrahydrofuranReflux
Stage #2: With sulfur dioxide In tetrahydrofuran at -30℃;
Stage #3: With sulfuryl dichloride In tetrahydrofuran at -40 - -30℃;
3. Synthesis of benzofuran-5-sulfonyl chloride. Isopropyl iodide (15.0 mmol) was added dropwise to a suspension of iodine (0.12 mmol), magnesium (30.0 mmol) in tetrahydrofuran (25 mL). After 15 min, a solution of 5- bromobenzofuran (15.2 mmol) in tetrahydrofuran (25 mL) was added dropwise and the reaction mixture was heated at reflux for 1 h. The mixture was cooled to -30 0C and sulfonyl chloride was bubbled through the reaction mixture for 10 min. The mixture was maintained for 30 min whereupon sulfuryl chloride (15.1 mmol) was added dropwise while cooling to -30 to -40 0C. The resulting solution was maintained for an additional 10 min and was allowed to warm to rt. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was diluted with dichloromethane (150 mL), washed with brine (3 x 100 mL), dried (sodium sulfate), and concentrated. The residue was purified by Flash chromatography (100/1 to 50/1 petroleum ether/ethyl acetate) to provide benzofuran-5-sulfonyl chloride in 15percent yield as a white solid. Data: 1H NMR (CDCl3) δ 8.37 (s, IH), 8.00 (d, IH), 7.84 (s, IH), 7.44 (d, IH), 6.97 (s, IH). LC/MS (ES) m/z 286 [M+BnH-l]+.
Reference: [1] Patent: WO2009/23844, 2009, A2, . Location in patent: Page/Page column 133-134
[2] Patent: WO2010/21797, 2010, A1, . Location in patent: Page/Page column 99
[3] Patent: WO2010/24980, 2010, A1, . Location in patent: Page/Page column 116; 117
  • 34
  • [ 23145-07-5 ]
  • [ 73183-34-3 ]
  • [ 519054-55-8 ]
YieldReaction ConditionsOperation in experiment
75% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 130℃; for 12 h; Inert atmosphere Under a nitrogen stream, 5-bromo-benzofuran (25g, 0.126mol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-(1,3,2-dioxaborolane) (38.67g, 0.152mol), Pd(dppf)Cl2 (3.11g, 3molpercent), KOAc (37.36g, 0.381mol) and 1,4-dioxane (500ml) were mixed, and the mixture was stirred for 12 hours at 130 °C. After completion of the reaction, and extracted with ethyl acetate, to remove water with MgSO4, KaramukuroMatogurafi By (hexane:: EA = 10 1 (v / v)), 2-(benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(23.23g, 75percent yield).
75% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 130℃; for 12 h; Inert atmosphere Under a nitrogen stream, 5-bromo-benzofuran (25g, 0.126mol), 4,4,4 ', 4', 5,5,5 ', 5'- octamethyl-2,2'-bi (1,3,2 - dioxaborolane) (38.67g, 0.152mol), Pd (dppf) Cl2 (3.11g, 3molpercent), KOAc (37.36g, 0.381mol), and 1,4-dioxane (500ml) was mixed , and the mixture was stirred for 12 hours at 130°C .After completion of the reaction, and extracted with ethyl acetate, to remove water with MgSO4, purified by column chromatography (hexane: EA = 10: 1 (v / v)) to give the 2- (benzofuran-5-yl) -4 to give the 4,5,5- tetramethyl-1,3,2-dioxaborolane (23.23g, 75percent yield).
75% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 130℃; for 12 h; Inert atmosphere Under a nitrogen stream, 5-bromobenzofuran (25 g, 0.126 mol), 4,4,4 ', 4,5,5,5,5-octamethyl-2,2'-bi (1,3,2-dioxaborolane) (38.67 g, 0.152 Dioxane (500 ml), and the mixture was stirred at 130 ° C for 12 hours. The reaction was terminated. The mixture was extracted with ethyl acetate, the water was removed with MgSO 4 and purified by column chromatography to obtain 23.23 g of benzofuran-5-yl) -4,4,5,5-etramethyl-1,3,2-dioxaborolane , Yield: 75percent).
75% With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 130℃; for 12 h; Inert atmosphere Under a nitrogen stream, 5-bromobenzofuran (25 g, 0.126 mol),2,2'-bi (1,3,2-dioxaborolane) (38.67 g, 0.152 mol), Pd (dppf) Cl2 (3.11 g, 3 molpercent), KOAc (37.36 g, 0.381 mol) and 1,4-dioxane (500 ml) were mixed and stirred at 130 ° C for 12 hours.After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO4,Purification by column chromatography (Hexane: EA = 10: 1 (v / v)) gave2- (benzofuran-5-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (23.23 g, yield 75percent).

Reference: [1] Patent: JP2016/40292, 2016, A, . Location in patent: Paragraph 0518-0520
[2] Patent: JP2015/527347, 2015, A, . Location in patent: Paragraph 0131; 0132
[3] Patent: KR101599586, 2016, B1, . Location in patent: Paragraph 0170-0174
[4] Patent: KR101879905, 2018, B1, . Location in patent: Paragraph 1187-1191
[5] Organometallics, 2016, vol. 35, # 10, p. 1559 - 1564
[6] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 607 - 610
[7] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 11030 - 11034[8] Angew. Chem., 2018, vol. 130, # 34, p. 11196 - 11200,5
[9] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003[10] Angew. Chem., 2018, # 130, p. 11165 - 11169,5
[11] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
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