[2-bromo-5-fluoro-4-(hydroxymethyl)phenyl]methanol

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

Procedure: (2-Bromo-5-fluoro-4-hydroxymethylphenyl)-methanol (71.3 mg, 0.303 mmol) was dissolved in tetrahydrofuran (1 mL), and 2-methoxypropene (214.7 mg, 2.97 mmol) was added thereto. The resultant mixture was cooled to 0° C., and then p-toluenesulfonic acid (1.0 mg. 0.0029 mmol) was added thereto. This mixture was stirred for 40 minutes, and then saturated aqueous sodium hydrogen carbonate was added. The resultant mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, to thereby obtain the titled compound (111.7 mg, 97%). The resultant mixture was extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: 5-Bromo-2-fluoro-4-hydroxymethyl-benzaldehyde (604.3 mg, 2.59 mmol) was dissolved in methanol (5 mL). To the resultant solution was added sodium borohydride (98.1 mg, 2.59 mmol) at 0° C. After stirring for 10 minutes, about 3 mL of methanol was removed by distillation. Water was added to the solution, and the resultant mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution methanol:dichloromethane (3:100)), to thereby obtain the titled compound (247.3 mg, 43%). about 3 mL of methanol was removed by distillation Water was added to the solution the resultant mixture was extracted with ethyl acetate The organic layer was concentrated under reduced pressure The resulting residue was purified by silica gel flash column chromatography (developing solution methanol:dichloromethane (3:100))

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

Procedure: (2-Bromo-5-fluoro-4-hydroxymethylphenyl)-methanol (71.3 mg, 0.303 mmol) was dissolved in tetrahydrofuran (1 mL), and 2-methoxypropene (214.7 mg, 2.97 mmol) was added thereto. The resultant mixture was cooled to 0° C., and then p-toluenesulfonic acid (1.0 mg. 0.0029 mmol) was added thereto. This mixture was stirred for 40 minutes, and then saturated aqueous sodium hydrogen carbonate was added. The resultant mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, to thereby obtain the titled compound (111.7 mg, 97%). The resultant mixture was extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: 5-Bromo-2-fluoro-4-hydroxymethyl-benzaldehyde (604.3 mg, 2.59 mmol) was dissolved in methanol (5 mL). To the resultant solution was added sodium borohydride (98.1 mg, 2.59 mmol) at 0° C. After stirring for 10 minutes, about 3 mL of methanol was removed by distillation. Water was added to the solution, and the resultant mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution methanol:dichloromethane (3:100)), to thereby obtain the titled compound (247.3 mg, 43%). about 3 mL of methanol was removed by distillation Water was added to the solution the resultant mixture was extracted with ethyl acetate The organic layer was concentrated under reduced pressure The resulting residue was purified by silica gel flash column chromatography (developing solution methanol:dichloromethane (3:100))

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

Procedure: (2-Bromo-5-fluoro-4-hydroxymethylphenyl)-methanol (71.3 mg, 0.303 mmol) was dissolved in tetrahydrofuran (1 mL), and 2-methoxypropene (214.7 mg, 2.97 mmol) was added thereto. The resultant mixture was cooled to 0° C., and then p-toluenesulfonic acid (1.0 mg. 0.0029 mmol) was added thereto. This mixture was stirred for 40 minutes, and then saturated aqueous sodium hydrogen carbonate was added. The resultant mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, to thereby obtain the titled compound (111.7 mg, 97%). The resultant mixture was extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: 5-Bromo-2-fluoro-4-hydroxymethyl-benzaldehyde (604.3 mg, 2.59 mmol) was dissolved in methanol (5 mL). To the resultant solution was added sodium borohydride (98.1 mg, 2.59 mmol) at 0° C. After stirring for 10 minutes, about 3 mL of methanol was removed by distillation. Water was added to the solution, and the resultant mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution methanol:dichloromethane (3:100)), to thereby obtain the titled compound (247.3 mg, 43%). about 3 mL of methanol was removed by distillation Water was added to the solution the resultant mixture was extracted with ethyl acetate The organic layer was concentrated under reduced pressure The resulting residue was purified by silica gel flash column chromatography (developing solution methanol:dichloromethane (3:100))