2-phenylmethoxyphenol

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:

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:

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(benzyloxy)phenol (4.2736 g, 21.34 mmol) and 2,5-dichloronitrobenzene (4.302 g, 22.41 mmol) in 40 mL of DMSO was added cesium carbonate (13.8 g, 42.7 mmol). The reaction was heated to 70° C. under argon for one hour, then cooled to room temperature. The solution was poured into EtOAc, washed with water, sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The titled product was obtained as a brown oil. cooled to room temperature washed with water, sat. aq. NaHCO3 and brine dried (Na2SO4) filtered concentrated in vacuo

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

Procedure: A solution of 2-benzyloxyphenol (6.01 g, 30 mmol) in anhydrous N,N-dimethylformamide (25 mL) was treated with anhydrous potassium carbonate (7.6 g, 55 mmol), then with 4-fluoronitrobenzene (3.53 g, 25 mmol), and heated to 90° C. for 5 h under nitrogen. The solution was cooled to room temperature, diluted with dichloromethane (50 mL), and treated with DOWEX® 550A OH anion exchange resin (10 g) which had been washed dry with methanol. The mixture was stirred for 3 h, filtered, and the filtrate concentrated in vacuo (exhaustively at end to remove DMF). The residue was chromatographed on silica gel (eluted with 2:1 hexane/ethyl acetate) to afford 4-(2-benzyloxyphenoxy)nitrobenzene (6.40 g, 66%) as a white solid. had been washed dry with methanol filtered the filtrate concentrated in vacuo (exhaustively at end to remove DMF) The residue was chromatographed on silica gel (eluted with 2:1 hexane/ethyl acetate)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: o-Benzyloxyphenol (7.5 g, 37.5 mmol) in dry DMF (60 mL) was treated with Me4N+OH-.5H2O (37.5 mmol, 6.8 g) followed by 2-bromothiazole (6.15 g, 37.5 mmol). The stirred solution was heated to about 100° C. under N2 (g) for 16 hours. The mixture was cooled in ice and crystalline, H2O-soluble Me4N+Br- was removed by filtration. The filtrate was concentrated in vacuo and partitioned between Et2O (100 mL) and H2O (60 mL). The organic phase was washed with 1N NaOH (3×) and brine, dried over Na2SO4 and concentrated in vacuo to afford 4.9 g of crude 2-(2-benzyloxyphenyl)thiazole (GCMS m/z 283 (M+)). This material was directly deprotected by treatment with 33% HBr in HOAc (35 mL) for 2 hours at about 20° C. The mixture was cooled in ice crystalline, H2O-soluble Me4N+Br- was removed by filtration The filtrate was concentrated in vacuo partitioned between Et2O (100 mL) and H2O (60 mL) The organic phase was washed with 1N NaOH (3×) and brine dried over Na2SO4 concentrated in vacuo

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

Procedure: A solution of 49.6 g (0.248 mole) of 2-benzyloxyphenol, 22.2 g (0.3 mole) of glycidol, 2 ml of pyridine and 150 ml of absolute ethanol was heated at reflux overnight. The dark solution was concentrated to give an oil which gradually crystallized. The solid was purified by column chromatography on 1.2 kg of silica gel eluted with 0-25% acetone in benzene. Appropriate fractions were combined and concentrated to yield 49.5 g (73%) of the title compound as a white solid, mp 84°-85° C. (carbon tetrachloride) (lit.1 mp 81°-82.5° C.). at reflux overnight The dark solution was concentrated to give an oil which gradually crystallized The solid was purified by column chromatography on 1.2 kg of silica gel eluted with 0-25% acetone in benzene concentrated