2-phenylpropan-2-yl 2-bromoacetate

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

Procedure: The sub-title compound was prepared analogously to the procedure described in Example 30(i) from 2-phenyl-2-propanol (3 g; 22 mmol) and bromacetylchloride (4.16 g, 26 mmol). Yield 1.2 g (44%).

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

Procedure: The sub-title compound was prepared analogously to the procedure described in Example 30(i) from 2-phenyl-2-propanol (3 g; 22 mmol) and bromacetylchloride (4.16 g, 26 mmol). Yield 1.2 g (44%).

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-(3-(2-(carboxymethoxy)-2-oxoethyl)-4-methoxyphenyl)dibenzothiophenium chloride (25 g, 59.2 mmol), 2-phenylpropan-2-yl 2-bromoacetate (15.2 g, 59.2 mmol), sodium iodide (17.7 g, 0.118 mmol), and cesium carbonate (38.4 g, 0.118 mmol) are dissolved in DMF (200 mL) and stirred at 25° C. for 4 h. The reaction mixture is quenched with water (500 mL), extracted with DCM (2×200 mL), the combined organic layers washed with water (4×200 mL), concentrated to a viscous oil and precipitated from MTBE (1 L) to afford the title compound as a white solid. The reaction mixture is quenched with water (500 mL) extracted with DCM (2×200 mL) the combined organic layers washed with water (4×200 mL) concentrated to a viscous oil precipitated from MTBE (1 L)

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-(3-(2-(carboxymethoxy)-2-oxoethyl)-4-methoxyphenyl)dibenzothiophenium chloride (25 g, 59.2 mmol), 2-phenylpropan-2-yl 2-bromoacetate (15.2 g, 59.2 mmol), sodium iodide (17.7 g, 0.118 mmol), and cesium carbonate (38.4 g, 0.118 mmol) are dissolved in DMF (200 mL) and stirred at 25° C. for 4 h. The reaction mixture is quenched with water (500 mL), extracted with DCM (2×200 mL), the combined organic layers washed with water (4×200 mL), concentrated to a viscous oil and precipitated from MTBE (1 L) to afford the title compound as a white solid. The reaction mixture is quenched with water (500 mL) extracted with DCM (2×200 mL) the combined organic layers washed with water (4×200 mL) concentrated to a viscous oil precipitated from MTBE (1 L)

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

Procedure: 2-phenylpropan-2-yl 2-bromoacetate (1.96 g, 7.63 mmol) was added to a solution of 5-(4-hydroxy-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium iodide (3.00 g, 6.94 mmol) and cesium carbonate (2.94 g, 9.02 mmol) in DMF (40 mL) at 0° C., warmed to r.t. and stirred overnight. The reaction mixture was diluted with water (200 mL) and washed with DCM (3×200 mL). The organic layers were washed with water (3×300 mL), concentrate and poured onto MTBE. The precipitate was filtered and dried to afford the title compound (3.80 g, 97%) as a white solid. 1H NMR (300 MHz, ((CD3)2SO) δ: 8.52 (d, J=7.5 Hz, 2H), 8.33 (d, J=7.5 Hz, 2H), 7.96 (t, J=7.2 Hz, 2H), 7.5 (d, J=7.9 Hz, 2H), 7.20-7.39 (m, 5H), 4.61 (s, 2H), 2.19 (s, 6H), 1.71 (s, 6H). washed with DCM (3×200 mL) The organic layers were washed with water (3×300 mL) concentrate poured onto MTBE The precipitate was filtered dried

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

Procedure: Pyridine (3.84 mL, 47.7 mmol) followed by bromoacetyl bromide (4.16 mL, 47.7 mmol) was added to a solution of 2-phenylpropan-2-ol (5.00 g, 36.7 mmol) in dichloromethane (100 mL) at 0° C., warmed to r.t. and stirred overnight. The reaction mixture was washed with water (3×100 mL), saturated aqueous sodium bicarbonate (3×100 mL), water (2×100 mL), dried (Na2SO4) and concentrated. The crude residue was purified by silica gel flash column chromatography (neutralized with TEA, heptanes) to afford the title compound (2.8 g (non-optimized), 30%) as a colorless oil. 1H NMR (300 MHz, ((CD3)2CO) δ: 7.44 (d, J=7.2 Hz, 2H), 7.34 (t, J=7.2 Hz, 2H), 7.25 (t, J=7.2 Hz, 1H), 4.01 (s, 2H), 1.78 (s, 6H). The reaction mixture was washed with water (3×100 mL), saturated aqueous sodium bicarbonate (3×100 mL), water (2×100 mL) dried (Na2SO4) concentrated The crude residue was purified by silica gel flash column chromatography (neutralized with TEA, heptanes)

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

Procedure: The sub-title compound was prepared analogously to the procedure described in Example 30(i) from 2-phenyl-2-propanol (3 g; 22 mmol) and bromacetylchloride (4.16 g, 26 mmol). Yield 1.2 g (44%).

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

Procedure: The sub-title compound was prepared analogously to the procedure described in Example 30(i) from 2-phenyl-2-propanol (3 g; 22 mmol) and bromacetylchloride (4.16 g, 26 mmol). Yield 1.2 g (44%).

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

Procedure: The sub-title compound was prepared analogously to the procedure described in Example 30(i) from 2-phenyl-2-propanol (3 g; 22 mmol) and bromacetylchloride (4.16 g, 26 mmol). Yield 1.2 g (44%).

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-(3-(2-(carboxymethoxy)-2-oxoethyl)-4-methoxyphenyl)dibenzothiophenium chloride (25 g, 59.2 mmol), 2-phenylpropan-2-yl 2-bromoacetate (15.2 g, 59.2 mmol), sodium iodide (17.7 g, 0.118 mmol), and cesium carbonate (38.4 g, 0.118 mmol) are dissolved in DMF (200 mL) and stirred at 25° C. for 4 h. The reaction mixture is quenched with water (500 mL), extracted with DCM (2×200 mL), the combined organic layers washed with water (4×200 mL), concentrated to a viscous oil and precipitated from MTBE (1 L) to afford the title compound as a white solid. The reaction mixture is quenched with water (500 mL) extracted with DCM (2×200 mL) the combined organic layers washed with water (4×200 mL) concentrated to a viscous oil precipitated from MTBE (1 L)