methyl 2-(2-fluorophenyl)propanoate

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: Methyl 2-(2-fluorophenyl)propanoate (26.2 g, 0.144 mol) was dissolved in THF (325 ml) and LiOH (1 M, 173 ml) added. The reaction mixture was stirred at room temperature for 2.5 h, before diluting with diethyl ether and extracting with water and 1N NaOH. The aqueous layer was acidified and extracted with ethyl acetate (×2). The organic extract was washed with brine, dried and evaporated to yield 2-(2-fluorophenyl)propanoic acid (22.5 g, 100%) as an oil. extracting with water and 1N NaOH extracted with ethyl acetate (×2) The organic extract was washed with brine dried evaporated

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

Procedure: Methyl 2-fluorophenylacetate (24.2 g, 0.144 mol) in THF (75 ml) was added dropwise over 20 min to a -78° C. solution of LDA (diisopropylamine (16.0 g, 0.158 mol) and n-butyl lithium (2.5 M, 61 ml)) in THF (300 ml) and stirring was continued for 1 h. Methyl iodide (22.5 g, 0.158 mol) was added dropwise over 15 min and the reaction mixture allowed to warm to room temperature over 1 h. The solution was poured into saturated ammonium chloride solution and extracted with diethyl ether. The extract was washed with brine, dried and evaporated to yield methyl 2-(2-fluorophenyl)propanoate (26.2 g, 100%) as an oil. extracted with diethyl ether The extract was washed with brine dried evaporated