(4-sulfanylphenyl)boronic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-mercaptophenylboronic acid (1.0 g, 90%, 5.84 mmol), 1-bromo-3-methoxypropane (1.83 g, 11.7 mmol), K2CO3 (2.45 g, 17.5 mmol) and catalytic amount of Nal in CH3CN (20 mL) was stirred at ambient temperature overnight. After CH3CN was removed, water was added to the residue, and the mixture was extracted with CH2Cl2. The combined organic extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give a milky oil. Water was added to this oily residue, and the aqueous layer was acidified to pH about 2 with concentrated HCl. The mixture was let stand at ambient temperature overnight, and the off-white solid was collected via filtration and washed with water and hexane to give 1.07 g (81%) of (4-{[3-(methoxy)propyl]thio}phenyl)boronic acid as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.98 (s, 2H), 7.68 (d, 2H, J=8.0 Hz), 7.22 (d, 2H, J=8.1 Hz), 3.38 (t, 2H, J=6.1 Hz), 3.19 (s, 3H), 2.98 (t, 2H, J=7.2 Hz), 1.85-1.70 (m, 2H); LRMS (ESI), m/z 225 (M−H). After CH3CN was removed water was added to the residue the mixture was extracted with CH2Cl2 The combined organic extract was washed with brine dried over Na2SO4 filtered the filtrate was concentrated to give a milky oil at ambient temperature overnight the off-white solid was collected via filtration washed with water and hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-mercaptophenylboronic acid (1.0 g, 90%, 5.84 mmol), 2-bromoacetamide (1.8 g, 13 mmol) and K2CO3 (2.70 g, 19.5 mmol) in CH3CN (20 mL) was stirred at ambient temperature overnight. After CH3CN was removed, water was added to the residue, and the solid was collected via filtration and washed with water to give 0.6 g (49%) of {4-[(2-amino-2-oxoethyl)thio]phenyl}boronic acid as a white solid. The boronic acid was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.00 (s, 2H), 7.68 (d, 2H, J=8.2 Hz), 7.55 (bs, 1H), 7.24 (d, 2H, J=8.2 Hz), 7.15 (bs, 1H), 3.61 (s, 2H); LRMS (APCI), m/z 210 (M−H). After CH3CN was removed water was added to the residue the solid was collected via filtration washed with water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-mercaptophenylboronic acid (1.0 g, 90%, 5.84 mmol), 1-bromo-2-methoxyethane (1.8 g, 13 mmol) and K2CO3 (2.70 g, 19.5 mmol) in CH3CN (20 mL) was stirred at ambient temperature overnight. After CH3CN was removed, water was added to the residue, and the solid was collected via filtration and washed with water to give 0.9 g of the crude (4-{[2-(methoxy)ethyl]thio}phenyl)boronic acid (75% pure by LC-MS). The crude boronic acid was used without further purification. After CH3CN was removed water was added to the residue the solid was collected via filtration washed with water

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4,4′-Dimethoxybenzhydrol (2.7 g, 11 mmol) and 4-mercaptophenylboronic acid (1.54 g, 10 mmol) were dissolved in 20 mL AcOH and heated at 60° C. for 1 h. Solvent was evaporated and the residue was dried under high vacuum. This material was used without further purification. Solvent was evaporated the residue was dried under high vacuum This material was used without further purification

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4,4′-Dimethoxybenzhydrol (2.7 g, 11 mmol) and 4-mercaptophenylboronic acid (1.54 g, 10 mmol) were dissolved in 20 mL AcOH and heated at 60° C. for 1 h. Solvent was evaporated and the residue was dried under high vacuum. This material was used without further purification. Solvent was evaporated the residue was dried under high vacuum This material was used without further purification

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4,4′-Dimethoxybenzhydrol (2.7 g, 11 mmol) and 4-mercaptophenylboronic acid (1.54 g, 10 mmol) were dissolved in 20 mL AcOH and heated at 60° C. for 1 h. Solvent was evaporated and the residue was dried under high vacuum. This material was used without further purification. Solvent was evaporated the residue was dried under high vacuum This material was used without further purification

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4,4′-Dimethoxybenzhydrol (2.7 g, 11 mmol) and 4-mercaptophenylboronic acid (1.54 g, 10 mmol) were dissolved in AcOH (20 mL) and heated at 60° C. for 1 h. Solvent was evaporated and the residue was dried under high vacuum. This material was used without further purification. Solvent was evaporated the residue was dried under high vacuum This material was used without further purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of (4-mercaptophenyl)boronic acid (0.847 g, 5.50 mmol), 2-(bromomethyl)benzonitrile (1.62 g, 8.25 mmol) and potassium carbonate (2.28 g, 16.5 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with hexane/ethyl acetate (2/1) and recrystallized from hexane/ethyl acetate to give the title compound (903 mg, yield 61%) as colorless crystals. washed twice with water and once with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was washed with hexane/ethyl acetate (2/1) recrystallized from hexane/ethyl acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of (4-mercaptophenyl)boronic acid (0.847 g, 5.50 mmol), 2-(bromomethyl)benzonitrile (1.62 g, 8.25 mmol) and potassium carbonate (2.28 g, 16.5 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with hexane/ethyl acetate (2/1) and recrystallized from hexane/ethyl acetate to give the title compound (903 mg, yield 61%) as colorless crystals. washed twice with water and once with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was washed with hexane/ethyl acetate (2/1) recrystallized from hexane/ethyl acetate