2-(2-chloro-6-fluorophenyl)ethanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-chloro-6-fluorophenyl)ethanol (500 mg, 2.87 mmol), was dissolved in dichloromethane (20 mL), and triethylamine (870 mg, 8.61 mmol) was added to the reaction mixture. The solution was cooled to 0° C. and methanesulfonyl chloride (492 mg, 4.31 mmol) was added slowly. After the addition was complete, the reaction was stirred at 0° C. for 15 min and at room temperature for 4 hours. Water was slowly added and the solution was extracted with dichloromethane. The organic layer was washed with brine, and dried over sodium sulfate and concentrated in vacuo to give the residue 2-chloro-6-fluorophenethyl methanesulfonate (52) as a clear oil. After the addition the solution was extracted with dichloromethane The organic layer was washed with brine dried over sodium sulfate concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-chloro-6-fluorophenyl)ethanol (500 mg, 2.87 mmol), was dissolved in dichloromethane (20 mL), and triethylamine (870 mg, 8.61 mmol) was added to the reaction mixture. The solution was cooled to 0° C. and methanesulfonyl chloride (492 mg, 4.31 mmol) was added slowly. After the addition was complete, the reaction was stirred at 0° C. for 15 min and at room temperature for 4 hours. Water was slowly added and the solution was extracted with dichloromethane. The organic layer was washed with brine, and dried over sodium sulfate and concentrated in vacuo to give the residue 2-chloro-6-fluorophenethyl methanesulfonate (52) as a clear oil. After the addition the solution was extracted with dichloromethane The organic layer was washed with brine dried over sodium sulfate concentrated in vacuo

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

Procedure: In analogy to the procedure described in example 78.1, 2-(2-chloro-6-fluoro-phenyl)-ethanol was reacted with ethyl iodoacetate in the presence of silver trifluoromethanesulfonate and 2,6-di-tert-butylpyridin to give [2-(2-chloro-6-fluoro-phenyl)-ethoxy]-acetic acid ethyl ester as colorless liquid. 1H NMR (CDCl3): 1.28 (t, J=7.1 Hz, 3H), 3.15 (t, J=7.1 Hz, 2H), 3.73 (t, J=7.3 Hz, 2H), 4.11 (s, 2H), 4.22 (q, J=7.1 Hz, 2H), 6.96 (m, 1H), 7.09-7.19 (m, 2H).