(3-Fluoro-4-methoxyphenyl)acetic acid

3-fluoro-4-methoxyphenylacetonitrile (42 g, 0.25 mol) was heated for 5 h with a solution of 32 g of potassium hydroxide in 120 mL of ethanol and 30 mL of water. After distillation of ethanol, the residue was diluted by water to a volume of 175 mL. The solution was filtered over the charcoal and the filtrate was acidified by 50percent HUnder nitrogen protection, (400 mg, 2.17 mmol) was dissolved in THF (4 mL). The reaction solution was cooled to 0oC. Lithium aluminium hydride (90.8 mg, 2.39 mmol) was added portionwise. The flask was then wrapped with aluminum foil and the resulting solution was stirred for 1 h at room temperature. The reaction was then quenched by the addition of 2 mL of water/ice. The resulting mixture was concentrated under vacuum. The solution was extracted with 2x10 mL of ethyl acetate and the organic layers were combined and evaporated. This afforded 290 mg (78%) of 2-(3-fluoro-4-methoxyphenyl)ethan-1-ol as colorless oil.General procedure: Triethylamine (1.4 mL) was added slowly to a solution of substituted phenyl acetic acid (5.0 mM) and benzaldehyde(5.0 mM) in acetic anhydride (1.4 mL). The reaction solution wasstirred for 7 h at 110 C. After cooling, the solution was acidified with concentrated hydrochloric acid, and then poured into icewater, stirred for 4 h. The resulting precipitate was collected and dissolved in 10% aqueous NaOH (5 mL). After washing with ethylacetate, the organic layers were separated. Hydrochloric acid wasadded to the aqueous phase until pH 3-4. The precipitated solidwas filtered and recrystallized from ethyl acetate to afford E-2, 3-diaryl acrylic acid. The yields were 39-85%.General procedure: To a solution of 7 (1.22 mmol) in DMF (2 mL), anhydrous K2CO3 (1.62 mmol) was first added, 6 (0.81 mmol) in DMF (2 mL) was then added dropwise, and the reaction mixture was stirred at 30 C for 3 h. When the reaction was completed, the mixture was diluted with water (20 mL) and extracted with EtOAc (25 mL x 3). The organic layer was washed with brine, dried over anhydrousNa2SO4, and concentrated under reduced pressure. The obtained residue was purified by silica gelchromatography to afford the desire product.To a mixture of 9 (45 g, 0.245 mol) in 500 mL toluene was added aluminium chloride (42.8 g, 0.32 mol) slowly to maintain the temperature not exceeding 25 C, The mixture was then boiled for 5 h and 260 mL of 10% HCl was added to the cooled solution. The precipitate was filtered off, the filtrate was extracted twice by 75 mL of 1, 2-dichloroethane and combined extracts were washed successively by 5% NaOH and water. The alkaline solution was combined with the precipitate and after adjusting pH to 12 by 5% NaOH, it was filtered over the charcoal and the filtrate was acidified by 50% H2SO4, The oil was extracted into ether and the extracts were evaporated after drying. The yield was 25 g (62%) of 3-fluoro-4-hydroxyphenylacetic acid. M.p. 109-111 C. MS (ESI) m/z (%): 193.0 [M+Na]+.

Molecular Weight:184.16
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:184.05357231
Monoisotopic Mass:184.05357231
Topological Polar Surface Area:46.5
Heavy Atom Count:13
Complexity:184
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes