* 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 bromine; acetic acid In chloroform at 20 - 78℃;
S1,willAnd thiophenethienothiophene(5 g, 35.7 mmol)Soluble in glacial acetic acid (36ml)And chloroform (10 ml)Of the mixed solvent,Br2 is added dropwise at room temperature(28.5 g, 180.56 mmol),Continue to stir for half an hour,And then heated to reflux at room temperature of 78 ° C overnight; Ling to room temperature, washed with water, precipitation of white solid compounds, and then washed with water and methanol 3 times, vacuum drying at room temperature,To give white solid compound 1, [M +] = 455.0 (yield: 95percent);
93%
Stage #1: With acetic acid In chloroform for 1 h; Inert atmosphere Stage #2: With bromine In chloroform for 1 h; Reflux
In the reactor into the thieno [3, 2 - b] thiophene (4.21 g, 30 mmol), under the protection of nitrogen, acetic acid is added into the reactor 30 ml, chloroform 50 ml, will be 20 mmol of Br2Solution is dripped slowly into the reaction in the reactor, stirring after 1 h, then gradually adding 15 mmol of Br2, Stirring 1 h, reflux overnight, cooled to the room temperature, to obtain the solid precipitation, successively de-ionized water and methanol washing, drying, the obtained crude product over silica gel column, to obtain compound C - 1 - 1 (12.72 g, 93percent).
91%
With bromine In chloroform at 60℃; for 24 h; Inert atmosphere
In an inert atmosphere, the bromine (9.2 ml; 28.5 g; 178.2 mmoles) diluted in 40 ml of chloroform is added to a solution of thienothiophene (5g; 35.7 mmoles) in 40 ml of chloroform, by slow dripping. The temperature is brought to 60°C. After 24 hours, it is brought to 20°C and a 1 M aqueous solution of sodium thiosulfate is added until the excess bromine is completely destroyed. The precipitate is filtered and washed first with water and then with chloroform. 14.6 g of 2,3,5,6-tetrabromothieno[3,2-b]thiophene of formula (VI) are obtained with a 91 percent yield:
Reference：
[1] Patent: CN106188090, 2016, A, . Location in patent: Paragraph 0086
[2] Patent: CN107056798, 2017, A, . Location in patent: Paragraph 0055; 0056; 0057
[3] Patent: WO2016/92065, 2016, A1, . Location in patent: Page/Page column 21
[4] Journal of Materials Chemistry C, 2018, vol. 6, # 16, p. 4471 - 4478
[5] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 5, p. 1547 - 1555
[6] J. Inst. Petr. Technol., 1935, vol. 21, p. 135,148
[7] Chemical Communications, 2005, # 9, p. 1161 - 1163
[8] Patent: US2009/43113, 2009, A1, . Location in patent: Page/Page column 6
[9] Chemistry - An Asian Journal, 2010, vol. 5, # 7, p. 1550 - 1554
[10] New Journal of Chemistry, 2013, vol. 37, # 4, p. 1189 - 1194
[11] Chemical Communications, 2015, vol. 51, # 60, p. 11961 - 11963
2
[ 1723-27-9 ]
[ 124638-53-5 ]
Reference：
[1] Advanced Functional Materials, 2012, vol. 22, # 1, p. 48 - 60
[2] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 22, p. 3465 - 3470
[3] Patent: CN103172646, 2016, B, . Location in patent: Paragraph 0111-0113
3
[ 25121-88-4 ]
[ 124638-53-5 ]
Reference：
[1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 22, p. 3465 - 3470
The reactor was charged with C-1 (9 · 12g, 20 mmol), acetic acid 500 ml, toluene 200 ml, Zn powder (2.62 g,(5.36g, 90percent) was obtained by filtration, and the solution was concentrated and filtered to give the compound C-28-1 (5.36g, 90percent). After the reaction was carried out, The * Synthesis of Intermediate C-28-2
80%
With zinc In acetic acid at 125℃; for 2.5 h; Inert atmosphere
In an inert atmosphere, the zinc powder (3.5g; 53.5 mmoles) is added in portions to the suspension of 2,3,5,6-tetrabromothieno[3,2-b]thiophene (14.6g; 32.2 mmoles) in 1 I of acetic acid. It is brought to 125°C. After 2 hours another portion of zinc is added (2.2g; 33.6 mmoles) and after 30 minutes another portion (0.8g; 12.2 mmoles). It is brought to 70°C and the zinc is removed by filtration. At 20°C, water is added to the filtrate and extracted with ethyl acetate. After washing the organic phase, first with a saturated aqueous solution of sodium bicarbonate and then to neutrality with water, it is dried over sodium sulfate. 7.6 g of 3,6-dibromothieno[3,2-b]thiophene of formula (V) are obtained with a 80percent yield:
76.6%
at 110℃; for 1 h; Large scale
Accurately weigh the glacial acetic acid (300. OKg) into a dry 500 L autoclave through a high-level tank.A solid 5 (64.0 OKg, 140.4 mol, L Oeq.) Was added to the kettle,Zinc dust (27. 0 Kg, 415.4 mol, 3. Oeq) was added.Heating to 110 ° C for 1 hour.The reaction was followed by HPLC,When the raw material disappears,The reaction was stopped.After the reaction was complete, the temperature was lowered to 40-50 ° C,The solvent acetic acid was distilled off under reduced pressure,To the basic no liquid,Cooled to room temperature,Ethyl acetate (300. OKg) was added,Stir for 30 minutes.Filtration, washing the solids with ethyl acetate (20. 0 KgX2)The filtrates were combined,Into the reactor,Water (300. OKg) was added to the reaction kettle,Stirred for 20 minutes,Allow to stand for 20 minutes(If it is difficult to liquid, you can filter liquid after the separation).The aqueous phase was separated,The organic phase was left in the reactor,The organic phase (300. OKgX) was washed with 6.6percent sodium hydroxide in water,So that the aqueous phase pH> 7, and then to the reactor into the water (200. OKg) washed once,The organic phase was dried over sodium sulfate (30. OKg) for 2 hours.The organic phase was concentrated,Dry out to dryness,Solvent free product 10 (31.4 kg, 76.6percent).
Reference：
[1] Patent: CN107056798, 2017, A, . Location in patent: Paragraph 0065; 0066; 0067
[2] Patent: WO2016/92065, 2016, A1, . Location in patent: Page/Page column 21; 22
[3] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 22, p. 3465 - 3470
[4] Patent: CN103172646, 2016, B, . Location in patent: Paragraph 0114-0116
[5] Chemical Communications, 2005, # 9, p. 1161 - 1163
[6] Organic and Biomolecular Chemistry, 2011, vol. 9, # 2, p. 588 - 595
[7] Chemistry - An Asian Journal, 2010, vol. 5, # 7, p. 1550 - 1554
[8] Patent: US9112157, 2015, B2,
With bromine; acetic acid; In chloroform; at 20 - 78℃;
S1,willAnd thiophenethienothiophene(5 g, 35.7 mmol)Soluble in glacial acetic acid (36ml)And chloroform (10 ml)Of the mixed solvent,Br2 is added dropwise at room temperature(28.5 g, 180.56 mmol),Continue to stir for half an hour,And then heated to reflux at room temperature of 78 C overnight; Ling to room temperature, washed with water, precipitation of white solid compounds, and then washed with water and methanol 3 times, vacuum drying at room temperature,To give white solid compound 1, [M +] = 455.0 (yield: 95%);
93%
In the reactor into the thieno [3, 2 - b] thiophene (4.21 g, 30 mmol), under the protection of nitrogen, acetic acid is added into the reactor 30 ml, chloroform 50 ml, will be 20 mmol of Br2Solution is dripped slowly into the reaction in the reactor, stirring after 1 h, then gradually adding 15 mmol of Br2, Stirring 1 h, reflux overnight, cooled to the room temperature, to obtain the solid precipitation, successively de-ionized water and methanol washing, drying, the obtained crude product over silica gel column, to obtain compound C - 1 - 1 (12.72 g, 93%).
91%
With bromine; In chloroform; at 60℃; for 24h;Inert atmosphere;
In an inert atmosphere, the bromine (9.2 ml; 28.5 g; 178.2 mmoles) diluted in 40 ml of chloroform is added to a solution of thienothiophene (5g; 35.7 mmoles) in 40 ml of chloroform, by slow dripping. The temperature is brought to 60C. After 24 hours, it is brought to 20C and a 1 M aqueous solution of sodium thiosulfate is added until the excess bromine is completely destroyed. The precipitate is filtered and washed first with water and then with chloroform. 14.6 g of 2,3,5,6-tetrabromo<strong>[251-41-2]thieno[3,2-b]thiophene</strong> of formula (VI) are obtained with a 91 % yield:
Synthesis of Compound 2Tetrabromothienothiophene was obtained by brominating thienothiophene using techniques developed by Iddon et al. (Lance S. Fuller, Brian Iddon, Kevin A. Smith J. Chem. Soc., Perkin Trans. 1, 1997, 34653470).Tetrabromo-<strong>[251-41-2]thieno[3,2-b]thiophene</strong> (2.0 g, 4.39 mmol) was dissolved in 50 ml of dry tetrahydrofuran (THF). The solution was cooled to -78 C. The cooled solution was slowly added with butyllithium (4 ml of 2.5 M in a hexane solution) and stirred for 30 min. Benzaldehyde (0.94 ml, 9.22 mmol) was slowly added in droplets. The solution was stirred overnight, allowing the temperature to gradually increase to room temperature. The solution was added with 50 ml of a saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, dried and concentrated under reduced pressure, yielding compound 2 (a white solid). Compound 2 was used directly in the following reaction without additional purification or separation.
With bromine; acetic acid; In water; for 4h;Inert atmosphere; Reflux; Large scale;
Under nitrogen protection,Intermediate 4 was added to a 2000 L autoclave(53. 2 Kg, calculated as 100% yield,Only 30Kg,The other for the water,162. 8 mol, 1. Oeq),Ac0H (1500. OKg).Start stirring,The temperature inside the reactor was raised to 50 to 55 C,Draw water (150. OKg),Keep the temperature at 50 ~ 55 C drop bromine(39.lKg, 244.4 mol, 1.5 eq.),After the dropwise addition, the reaction was continued for 1 hour with stirring.Heated to reflux,Close the exhaust valve,Maintain the dropping under refluxBromine(130. 3 Kg, 814.4 mol, 5. Oeq).After the dropwise addition,The reaction was stirred for 3 hours.Sampling monitoring,Until the tribromo intermediate has been less than 10%.Stirring down to 70 C for hot filtration.The filter cake was washed with water (30. OKg) until the filtrate had no color,Dried and dried to give an off-white solid (52. OKg, water content 14%, yield 60.4%). [0114] Step 5:
The reactor was charged with C-1 (9 · 12g, 20 mmol), acetic acid 500 ml, toluene 200 ml, Zn powder (2.62 g,(5.36g, 90%) was obtained by filtration, and the solution was concentrated and filtered to give the compound C-28-1 (5.36g, 90%). After the reaction was carried out, The * Synthesis of Intermediate C-28-2
80%
With zinc; In acetic acid; at 125℃; for 2.5h;Inert atmosphere;
In an inert atmosphere, the zinc powder (3.5g; 53.5 mmoles) is added in portions to the suspension of 2,3,5,6-tetrabromothieno[3,2-b]thiophene (14.6g; 32.2 mmoles) in 1 I of acetic acid. It is brought to 125C. After 2 hours another portion of zinc is added (2.2g; 33.6 mmoles) and after 30 minutes another portion (0.8g; 12.2 mmoles). It is brought to 70C and the zinc is removed by filtration. At 20C, water is added to the filtrate and extracted with ethyl acetate. After washing the organic phase, first with a saturated aqueous solution of sodium bicarbonate and then to neutrality with water, it is dried over sodium sulfate. 7.6 g of 3,6-dibromothieno[3,2-b]thiophene of formula (V) are obtained with a 80% yield:
76.6%
With acetic acid; zinc; at 110℃; for 1h;Large scale;
Accurately weigh the glacial acetic acid (300. OKg) into a dry 500 L autoclave through a high-level tank.A solid 5 (64.0 OKg, 140.4 mol, L Oeq.) Was added to the kettle,Zinc dust (27. 0 Kg, 415.4 mol, 3. Oeq) was added.Heating to 110 C for 1 hour.The reaction was followed by HPLC,When the raw material disappears,The reaction was stopped.After the reaction was complete, the temperature was lowered to 40-50 C,The solvent acetic acid was distilled off under reduced pressure,To the basic no liquid,Cooled to room temperature,Ethyl acetate (300. OKg) was added,Stir for 30 minutes.Filtration, washing the solids with ethyl acetate (20. 0 KgX2)The filtrates were combined,Into the reactor,Water (300. OKg) was added to the reaction kettle,Stirred for 20 minutes,Allow to stand for 20 minutes(If it is difficult to liquid, you can filter liquid after the separation).The aqueous phase was separated,The organic phase was left in the reactor,The organic phase (300. OKgX) was washed with 6.6% sodium hydroxide in water,So that the aqueous phase pH> 7, and then to the reactor into the water (200. OKg) washed once,The organic phase was dried over sodium sulfate (30. OKg) for 2 hours.The organic phase was concentrated,Dry out to dryness,Solvent free product 10 (31.4 kg, 76.6%).
In methanol; chloroform; water; acetic acid; toluene;
3,6-dibromothieno[3,2-b]thiophene Synthesis Procedures: A 1 L three-neck round bottom flask equipped with a reflux condenser was charged with perbromothieno[3,2-b]thiophene (30.0 g, 0.0658 mol) then glacial acetic acid (150 mL) via syringe. White solids remained undissolved in the clear solution. This solution was heated to 100 C. via oil bath and permitted to stir at this temperature for 30 minutes. Then, zinc dust (4.15 g, 0.0635 mol) was added. The reaction was permitted to stir at 100 C. for 1 hour, and then reaction completion was monitored via GC-MS. It indicated the presence of mono-, di-, tri-, and tetra-brominated product. More Zn dust (13.25 g, 0.2027 mol) was added in five portions over a 5 hour and 30 minute interval. It is also important to note that anhydrous toluene (100 mL) was added to the 500 mL three-neck round bottom flask after portion two of Zn dust was added. Even at the 5 hour and 30 minute point, GC-MS still indicated the presence of mono-, di-, tri-, and tetra-brominated product. Let the reaction cool to room temperature, then filtered it through a Buchner funnel. The solids were rinsed with toluene until no spotting observed on TLC. The filtrate was transferred to a 2 L separatory funnel that contained deionized water (600 mL). NaCl was added along with additional chloroform (100 mL) to help break up the slight emulsion that formed. The organic layer/slight emulsion and aqueous layer were separated. The aqueous layer was back-extracted with chloroform (1*300 mL, 1*200 mL). The organic layer was washed with basic deionized water (4*700 mL) then deionized water (1*700 mL). The organic layer was filtered through a Buchner funnel to remove any residual salts and/or zinc, and then solvents were removed via rotary evaporation. Methanol (100 mL) was added to the 1 L single-neck round bottom flask that contained the product and the solution was stirred and cooled to 0 C. via ice-water bath. The solution was stirred at 0 C. for 30 minutes, and then cooled to -35 C. to ensure maximum product precipitation. It was then filtered through a Buchner tunnel and the product was dried under vacuum. Product obtained: 16.62 g.
Stage #1: tetrabromo-thieno[3,2-b]thiophene With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.166667 - 0.333333h;
Stage #2: undecylaldehyde In tetrahydrofuran; hexanes at -78 - 20℃;
Stage #3: With water In tetrahydrofuran; hexanes
4
FIG. 13 is a reaction scheme showing the synthesis of 3,7-didecylthieno[3,2- b]thieno[2',3':4,5]thieno[2,3-T]thiophene according to Example 4; 2,3,4,5- tetrabromothieno[3,2-]thiophene (71) was prepared according to Fuller et al., J. Chem. Soc, Perkin Trans, 1, 1997, 3465, which is hereby incorporated herein by reference. To a mixture of compound 71 (40.0 g, 0.088 mol) in 300 mL dry THF, butyllithium (70 mL, 0.175 mol, 2.5 M in hexanes) was added dropwise at -78 0C. The resulting mixture was stirred another 10 to 20 minutes and undecyl aldehyde (30.0 g, 0.176 mol) was added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. Water (20 mL) was added, and the solvent was removed by evaporation. The residue was mixed with hexane (300 mL) and the resultant solid was collected by filtration. This solid then was dried under vacuum, yielding compound 72 that was sufficiently pure for subsequent reaction (47.0 g, 83.9% yield). M.p. 116.0-118.00C. 1H NMR (CD2Cl2) δ 5.15(m, 2H), 2.31(broad, 2H), 1.91(m, 4H), 1.31(m, 32H), 0.92(t, 6H). 13C NMR: 144.06, 109.05, 70.58, 38.77, 32.36, 30.06, 30.04, 29.99, 29.77, 29.65, 26.09, 23.12, 14.29.
83.9%
Stage #1: tetrabromo-thieno[3,2-b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: undecylaldehyde In tetrahydrofuran; hexane at 20℃;
Stage #3: With water In tetrahydrofuran; hexane
4
2,4-di(l-hydroxydecyl)-3,6-dibromothieno[3,2-6]thiophene (72). 2,3,4,5-tetrabromothieno[3,2-Z?]thiophene (71) is prepared according to Fuller et al., 1 J. CHEM. SOC, PERKIN TRANS, 3465 (1997), which is hereby incorporated herein by reference. Butyllithium (70 mL, 0.175 mol, 2.5 M in hexanes) is added dropwise at -78 °C to a mixture of compound 71 (40.0 g, 0.088 mol) in 300 mL dry THF. The resulting mixture is stirred another 10 to 20 minutes and undecyl aldehyde (30.0 g, 0.176 mol) is added dropwise. The mixture is allowed to warm to room temperature and stirred overnight. Water (20 mL) is added, and the solvent is removed by evaporation. The residue is mixed with hexane (300 mL) and the resultant solid is collected by filtration. This solid then is dried under vacuum, yielding compound 72 that is sufficiently pure for subsequent reaction (47.0 g, 83.9% yield). M.P. : 116.0- 118.0 °C. ¾ NMR (CD2CI2): δ 5.15(m, 2H), 2.31 (broad, 2H), 1.91(m, 4H), 1.3 l(m, 32H), 0.92(t, 6H). 13C NMR: 144.06, 109.05, 70.58, 38.77, 32.36, 30.06, 30.04, 29.99, 29.77, 29.65, 26.09, 23.12, 14.29.
Stage #1: tetrabromo-thieno[3,2-b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: undecylaldehyde In tetrahydrofuran; hexane at 20℃;
2,5-di(1-hydroxydecyl)-3,6-dibromothieno[3,2-b]thiophene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83.9%
Stage #1: tetrabromo-thieno[3,2-b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667 - 0.333333h;
Stage #2: undecylaldehyde In tetrahydrofuran; hexane at -78 - 20℃;
4
2,4-di(l-hydroxydecyl)-3,6-dibromothieno[3,2-£]thiophene (72).; 2,3,4,5- tetrabromothieno[3,2-&]thiophene (71) was prepared according to Fuller et al., J. Chem. Soc, Perkin Trans, 1, 1997, 3465, which is hereby incorporated herein by reference. To a mixture of compound 71 (40.0 g, 0.088 mol) in 300 mL dry THF, butyllithium (70 mL, 0.175 mol, 2.5 M in hexanes) was added dropwise at -78 °C. The resulting mixture was stirred another 10 to 20 minutes and undecyl aldehyde (30.0 g, 0.176 mol) was added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. Water (20 mL) was added, and the solvent was removed by evaporation. The residue was mixed with hexane (300 mL) and the resultant solid was collected by filtration. This solid then was dried under vacuum, yielding compound 71 that was sufficiently pure for subsequent reaction (47.0 g, 83.9% yield). M.p. 116.0-118.00C. 1H NMR (CD2Cl2) δ 5.15(m, 2H), 2.31(broad, 2H), 1.91(m, 4H), 1.31(m, 32H), 0.92(t, 6H). 13C NMR: 144.06, 109.05, 70.58, 38.77, 32.36, 30.06, 30.04, 29.99, 29.77, 29.65, 26.09, 23.12, 14.29.
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 60 - 110℃;Inert atmosphere;
General procedure: Toluene wasdegassed by exchanging between vacuum and a stream ofargon (3 ×). 2,3,5,6-Tetrabromothieno[3,2-b]thiophene(1.0 equiv) and Pd(Ph3P)4 (0.05-0.10 equiv) were dissolvedin this degassed toluene (4 mL) at 60-70 C. To the obtainedsolution H2O (1 mL), K3PO4 (2.0 equiv), and arylboronicacid (1.2 equiv) were added. The reaction was vigorouslystirred under argon atmosphere at 110 C until TLC (100%hexane) showed the complete consumption of the startingmaterial. The reaction mixture was filtered to removeinsoluble particles. The filtrate was washed several timeswith H2O, dried over Na2SO4 and concentrated underreduced pressure by rotary evaporation. The residue waspurified by SiO2 column chromatography (100% hexane) togive the product as a white solid. In case of alkoxyphenylboronic acid, 1,4-dioxane was used instead of toluene (ref.6b). In fact, toluene-H2O gave the same result. 2,3,6-Tribromo-5-phenylthieno[3,2-b]thiophene (2a): Startingfrom 1 (230 mg, 0.5 mmol) and phenylboronic acid (74 mg,0.6 mmol), 2a was isolated (191 mg, 51%) as white crystals;mp 132-133 C. 1H NMR (500 MHz, CDCl3): delta = 7.68 (m,2 H, Ar), 7.45 (m, 3 H, Ar). 13C NMR (500 MHz, CDCl3):delta = 99.8, 106.9, 112.5, 128.8, 128.9, 129.0, 132.4, 136.4,139.8. IR (KBr): 3083 (m), 2929 (s), 2905 (m), 1658 (m),1610 (m), 1582 (m), 743 (s), 684 (s), 588 (m) cm-1. HRMS(EI, 70 eV): m/z (M+, [79Br,79Br,79Br]) calcd for C12H5Br3S2:449.7383; found: 449.7392.
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 60 - 110℃; Inert atmosphere; regioselective reaction;
General Procedure for the Synthesis of 2-Aryl-3,5,6-tribromothieno[3,2-b]thiophene 2a-j:
General procedure: Toluene wasdegassed by exchanging between vacuum and a stream ofargon (3 ×). 2,3,5,6-Tetrabromothieno[3,2-b]thiophene(1.0 equiv) and Pd(Ph3P)4 (0.05-0.10 equiv) were dissolvedin this degassed toluene (4 mL) at 60-70 °C. To the obtainedsolution H2O (1 mL), K3PO4 (2.0 equiv), and arylboronicacid (1.2 equiv) were added. The reaction was vigorouslystirred under argon atmosphere at 110 °C until TLC (100%hexane) showed the complete consumption of the startingmaterial. The reaction mixture was filtered to removeinsoluble particles. The filtrate was washed several timeswith H2O, dried over Na2SO4 and concentrated underreduced pressure by rotary evaporation. The residue waspurified by SiO2 column chromatography (100% hexane) togive the product as a white solid. In case of alkoxyphenylboronic acid, 1,4-dioxane was used instead of toluene (ref.6b). In fact, toluene-H2O gave the same result.
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 60 - 110℃;Inert atmosphere;
General procedure: Toluene wasdegassed by exchanging between vacuum and a stream ofargon (3 ×). 2,3,5,6-Tetrabromothieno[3,2-b]thiophene(1.0 equiv) and Pd(Ph3P)4 (0.05-0.10 equiv) were dissolvedin this degassed toluene (4 mL) at 60-70 C. To the obtainedsolution H2O (1 mL), K3PO4 (2.0 equiv), and arylboronicacid (1.2 equiv) were added. The reaction was vigorouslystirred under argon atmosphere at 110 C until TLC (100%hexane) showed the complete consumption of the startingmaterial. The reaction mixture was filtered to removeinsoluble particles. The filtrate was washed several timeswith H2O, dried over Na2SO4 and concentrated underreduced pressure by rotary evaporation. The residue waspurified by SiO2 column chromatography (100% hexane) togive the product as a white solid. In case of alkoxyphenylboronic acid, 1,4-dioxane was used instead of toluene (ref.6b). In fact, toluene-H2O gave the same result.
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