ChemicalBook CAS DataBase List (3-CHLORO-4-FLUOROPHENOXY)ACETIC ACID

(3-CHLORO-4-FLUOROPHENOXY)ACETIC ACID synthesis

5synthesis methods

Product Name:(3-CHLORO-4-FLUOROPHENOXY)ACETIC ACID
CAS Number:331-40-8
Molecular formula:C8H6ClFO3
Molecular Weight:204.58

2613-23-2 Synthesis

2613-23-2
191 suppliers
$8.00/5g

96-32-2
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$15.00/5g

331-40-8
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$57.50/250mg

Yield:331-40-8 79%

Reaction Conditions:

Stage #1: 3-chloro-4-fluorophenolwith potassium hydroxide in dimethyl sulfoxide at 20; for 0.166667 h;
Stage #2: bromoacetic acid methyl ester in dimethyl sulfoxide at 0 - 20;
Stage #3: with hydrogenchloride;watermore than 3 stages;

Steps:

1

To a stirring solution of finely ground KOH (1.2 g, 20.4 mmol) in DMSO (6 mL) was added 3-chloro-4-fluorophenol (1.0 g, 6.8 mmol). The mixture was stirred for 10 minutes at RT, then cooled to 0° C. Methyl bromoacetate (1.25 g, 8.2 mmol) was added, and the reaction was slowly warmed to RT and stirred overnight. H₂O (10 mL) and MeOH (10 mL) were added to the mixture, and the reaction was stirred for 1 h. After removing MeOH under reduced pressure, H₂O (100 mL) and Et₂O (50 mL) were added, and the layers were separated. The aqueous phase was acidified to pH 2 with an aqueous concentrated HCl solution and extracted with CH₂Cl₂(200 mL). The organic layer was dried over MgSO₄, filtered, concentrated, and dried to give 2-(3-chloro-4-fluorophenoxy)acetic acid as a white solid (1.1 g, 79%). ¹H NMR (400 MHz, CDCl₃) δ 7.10 (t, J=8.8 Hz, 1H), 7.01-6.98 (m, 1H), 6.84-6.80 (m, 1H), 4.68 (s, 2H).

References:

US2008/27067,2008,A1 Location in patent:Page/Page column 263