(3-BROMO-PHENOXY)-ACETIC ACID

2) OA: 2-(5-Bromo-2-methoxyphenoxy)acetic acid j00260j 3 -Bromophenol (1.0 g, 5.78 mmol) and bromoacetic acid (0.803 g, 5.78 mmol) were dissolved in THF (28.9 mL). NaH (0.305 g, 12.72 mmol) was added portionwise over the course of 10 minutes. The reaction was then heated to reflux andallowed to stir overnight. The reaction was cooled to ambient temperature and quenched with water. The THF was concentrated in vacuo and the residue diluted with water and EtOAc. The aqueous layer was acidified with HC1 and extracted with EtOAc. The organic layer was further washed with water, washed with brine, dried (Na2504), filtered, and concentrated in vacuo to yield Example 1OA (869 mg, 65percent yield). ‘H NMR(400MHz, METHANOL-d4) ö 7.22 - 7.17 (m, 1H), 7.13 - 7.10 (m, 2H), 6.91 (ddd, J=8.3, 2.4, 1.1 Hz, 1H), 4.67 (s, 2H)General procedure: An appropriately substituted phenol (50 mmol) was added to a solution of NaOH (187.5 mmol) in 15 mL of H2O. Chloroacetic acid (85 mmol) was added slowly at to the resulting solution at 40 C and the reaction mixture was heated to 85 C. Stirring was continued for 2 h, the reaction was cooled to room temperature and 100 mL H2O was added. The reaction was filtered and the filtrate was acidified with concentrated HCl to pH 1-2. The brown oil fraction which formed was extracted to diethylether (2 × 50 ml). The ether fraction, in turn, was extracted with an aqueous solution of 5% Na2CO3 (2 × 37.5 ml). The combined Na2CO3 fractions were acidified to pH 1-2 with concentrated HCl and the resulting precipitate was collected by filtration and oven dried to obtain the required acids.24General procedure: Equimolar quantities of 2-chloro acetic acid/3-chloro propionicacid (0.05 mol) and appropriate phenol (1a-q) (0.05 mol) were taken in a conical flask, to which aqueous solution of NaOH(0.12 mol in 25 mL water) was slowly added with constant stirring.The solution was stirred for 2 h until the solution turned clear, brown or yellow and then the reaction mixture was evaporatedin a evaporating dish until the solid sodium salt was precipitated. The salt was isolated, dried, dissolved in water and acidified byadding con. HCl. The precipitated aryloxy acetic/propionic acidwas filtered and recrystallized from water or ethanolGeneral procedure: General procedure: To a solution of phenol or ring-substituted phenol (20 mmol) in water (20 mL) was added sodium chloroacetate (22 mmol) at rt. The mixture was heated and stirred at reflux for 8 h. The reaction mixture was cooled and the pH was adjusted to a value of 1.0 with 5 N HCl. The solution was filtered and the obtained solid was recrystallized from dehydrated ethanol to afford the pure product. 3-Bromophenoxyacetic acid (1o) Following the general proceduret he compound 1o was obtained in 62 % yield as a white solid. m.p. 108-110 C. 1H NMR (400 MHz, CDCl3) delta7.21-7.06 (m, 3H), 6.86 (dt, J = 7.2, 2.3 Hz, 1H), 4.64 (s, 2H). MS (ESI) m/z: 230 [M-H]-. (S10)General procedure: A mixture of benzoic acid (50 mmol), N-aminothiourea(50 mmol) and POCl3 (13 mL) was heated at 75 C for 0.5 h. Themixture was cooled to which water (10 mL) was added and thereaction mixture was refluxed for 4 h. The mixture was cooled and pH was adjusted to 8.0 by adding 50% sodium hydroxide solution.The separated solid was filtered and recrystallized from ethanolto give desired compounds.

Molecular Weight:231.04
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:229.95786
Monoisotopic Mass:229.95786
Topological Polar Surface Area:46.5
Heavy Atom Count:12
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes