(3,4-Difluorophenyl)acetic acid

beige crystalline needles

3 -(3-(3-(To (Step A. (2-(Step A: 5-(General procedure: To the various carboxylic acids (obtained from ASDI, Inc., 0.076 mmol, 1 equiv.) was added dry DCM (0.5 mL), oxalyl chloride (0.076 mmol, 1 equiv.), and then 2 drops of DMF. The reactions were placed in the shaker and reacted overnight at ambient temperature for 24 h. A solution of the hydrochloride salt of 3 (0.048 mmol, 1 equiv.) in 1.5 mL of DMF was added, followed by DIEA (0.240 mmol, 5 equiv.). The vials were agitated in the shaker for 24 h at ambient temperature. The solvent was removed in a Genevac HT24 centrifugal evaporator, and the crude intermediates were carried forward without purification. To each of the above crude products was added 10% TEA in MeOH (2 mL). The reaction vials were then placed in the shaker at 33 C overnight, and the solvent was evaporated. All the crude products were purified via preparative HPLC to >95% purity, and the desired products in the yields as described below.Step A General procedure: SOCl2 (1.65 mL) was added to a solution of benzoic or phenylaceticacid derivatives (2 mmol) in dry CH2Cl2 (1.65 mL), and thesuspension was refluxed for 4 h. The resulting solution was evaporated, the residue was dissolved in dry acetone (10 mL) and 3-(4-aminophenyl)-7-hydroxy-coumarin 4 (0.51 g, 2 mmol) was added.The mixture was refluxed with anhydrous K2CO3 (1.104 g, 8 mmol)for 4 h. Acetone was removed under reduced pressure and coldwater (20 mL) was added. 3 N HCl was added until the solutionbecame acidic. The resulting precipitate was filtered, washed withwater and recrystallized from methanol or ethanol to give thedesired products 5a-k.To a stirred solution of 2- (3, 4-difluorophenyl) acetic acid (5 g, 29 mmol) in MeOH (50 mL) was added SOCl2(3 mL, 116 mmol) , the reaction mixture was stirred for 5 hrs at 65 C. Most of solvent was removed and this residue was dissolved by H2O (50 mL) , then adjusted to pH = 7 8 with aq. NaHCO3 and extracted with EtOAc (50 mL x 3) . The combined organic layers were washed with brine, dried over Na2SO4, concentrated to give methyl 2- (3, 4-difluorophenyl) acetate (4.5 g, crude) as yellow oil. MS: M/e 1877 (M+1)+.

Intermediate for medicine, pesticide, liquid crystal material.

Molecular Weight:172.13
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:172.03358575
Monoisotopic Mass:172.03358575
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:172
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes