3-bromo-4-phenylmethoxyphenol

Conditions: temp:72.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a chilled solution of phenol (Step 1) (4.7 g, 16.8 mmole) in ACN was added MgCl2 (1.92 g, 20 mmole) portion-wise while maintaining the temperature below 10° C., followed by paraformaldehyde (2.52 g, 84 mmole) and TEA (9.5 mL, 67 mmole) producing a 15° C. exotherm. The mixture was heated to 72° C. for 2 hrs. The reaction was cooled to room temperature and poured into saturated aqueous ammonium chloride (500 mL), extracted with ethyl acetate (2×150 mL). The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 5% ethyl acetate/hexane). ESLRMS m/z 306.9 (M+H). while maintaining the temperature below 10° C. producing a 15° C. exotherm The reaction was cooled to room temperature extracted with ethyl acetate (2×150 mL) The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL) dried over Na2SO4 filtered concentrated in vacuo

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

Procedure: To a mixture of MeOH (50 mL) and K2CO3 (49.36 g, 357 mmole) at r.t was dripped commercially available 2-bromobenzene-1,4-diol (15 g, 79 mmole) in MeOH (25 mL), followed by the syringe addition of benzyl bromide (14.93 g, 10.38 mL). The resulting mixture was refluxed for 8 hours. The reaction was cooled to RT and poured into saturated aqueous ammonium chloride (500 mL) and extracted with ethyl acetate (2×150). The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 10% Ethyl acetate/Hexane). ESLRMS m/z 280.9 (M+H). The resulting mixture was refluxed for 8 hours extracted with ethyl acetate (2×150) The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL) dried over Na2SO4 filtered concentrated in vacuo

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

Procedure: To a mixture of MeOH (50 mL) and K2CO3 (49.36 g, 357 mmole) at r.t was dripped commercially available 2-bromobenzene-1,4-diol (15 g, 79 mmole) in MeOH (25 mL), followed by the syringe addition of benzyl bromide (14.93 g, 10.38 mL). The resulting mixture was refluxed for 8 hours. The reaction was cooled to RT and poured into saturated aqueous ammonium chloride (500 mL) and extracted with ethyl acetate (2×150). The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 10% Ethyl acetate/Hexane). ESLRMS m/z 280.9 (M+H). The resulting mixture was refluxed for 8 hours extracted with ethyl acetate (2×150) The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL) dried over Na2SO4 filtered concentrated in vacuo

Conditions: temp:72.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a chilled solution of phenol (Step 1) (4.7 g, 16.8 mmole) in ACN was added MgCl2 (1.92 g, 20 mmole) portion-wise while maintaining the temperature below 10° C., followed by paraformaldehyde (2.52 g, 84 mmole) and TEA (9.5 mL, 67 mmole) producing a 15° C. exotherm. The mixture was heated to 72° C. for 2 hrs. The reaction was cooled to room temperature and poured into saturated aqueous ammonium chloride (500 mL), extracted with ethyl acetate (2×150 mL). The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 5% ethyl acetate/hexane). ESLRMS m/z 306.9 (M+H). while maintaining the temperature below 10° C. producing a 15° C. exotherm The reaction was cooled to room temperature extracted with ethyl acetate (2×150 mL) The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL) dried over Na2SO4 filtered concentrated in vacuo

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

Procedure: To a mixture of MeOH (50 mL) and K2CO3 (49.36 g, 357 mmole) at r.t was dripped commercially available 2-bromobenzene-1,4-diol (15 g, 79 mmole) in MeOH (25 mL), followed by the syringe addition of benzyl bromide (14.93 g, 10.38 mL). The resulting mixture was refluxed for 8 hours. The reaction was cooled to RT and poured into saturated aqueous ammonium chloride (500 mL) and extracted with ethyl acetate (2×150). The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 10% Ethyl acetate/Hexane). ESLRMS m/z 280.9 (M+H). The resulting mixture was refluxed for 8 hours extracted with ethyl acetate (2×150) The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL) dried over Na2SO4 filtered concentrated in vacuo