3-Fluoro-2-methoxybenzenemethanol

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: In an analogous manner to that described in (γ) (3-fluoro-2-methoxy-phenyl)-methanol was treated with mesylchloride to obtain 1-chloromethyl-3-fluoro-2-methoxy-benzene as a colorless liquid; MS: 174 (M)+.

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

Procedure: In an analogous manner to that described in (γ) (3-fluoro-2-methoxy-phenyl)-methanol was treated with mesylchloride to obtain 1-chloromethyl-3-fluoro-2-methoxy-benzene as a colorless liquid; MS: 174 (M)+.

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

Procedure: In an analogous manner to that described in (α) 2-fluoro-6-hydroxymethyl-phenol was alkylated with methyliodide to yield (3-fluoro-2-methoxy-phenyl)-methanol as a white solid; MS: 142 (M)+.

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

Procedure: A solution of (3-fluoro-2-methoxyphenyl)methanol (3.02 g, 19.3 mmol) and triethylamine (6.74 mL, 48.4 mmol) in dichloromethane (20 mL) is treated with methanesulfonyl chloride (2.99 mL, 38.7 mmol) slowly at room temperature and stirred under nitrogen for 3 h. The reaction is the diluted with diethyl ether, washed with 0.5 M hydrochloric acid twice, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the title compound as a yellow oil (2.71 g, 80%). 1H NMR (400 MHz, CDCl3) δ 7.15-6.93 (m, 3H), 4.61 (s, 2H), 4.00 (s, 3H). washed with 0.5 M hydrochloric acid twice dried over anhydrous sodium sulfate filtered concentrated

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

Procedure: To a solution of 3-fluoro-2-methoxy-benzaldehyde (3.41 g, 22.1 mmol) in methanol (20 mL) is slowly added portionwise sodium borohydride (1.00 g, 26.6 mmol). The reaction is stirred at room temperature under nitrogen overnight. The reaction is diluted with diethyl ether, washed with water twice, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3.02 g (87%) of the title compound as a clear colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.09-6.92 (m, 3H), 4.65 (d, 2H), 3.97 (s, 3H), 2.14 (t, 1H, OH). washed with water twice dried over anhydrous sodium sulfate filtered concentrated

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 solution of 3-fluoro-2-methoxy-benzenemethanol (WO 20000419) (0.50 g) and thionyl chloride (0.47 ml) in dichloromethane (30 ml) was stirred for 2 hours then concentrated in-vacuo to give the subtitled compound, which was used directly in the next step. then concentrated in-vacuo

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

Procedure: In an analogous manner to that described in (γ) (3-fluoro-2-methoxy-phenyl)-methanol was treated with mesylchloride to obtain 1-chloromethyl-3-fluoro-2-methoxy-benzene as a colorless liquid; MS: 174 (M)+.