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ChemicalBook CAS DataBase List 3-CHLORO-4-(3-CHLOROPHENOXY)ANILINE
84865-99-6

3-CHLORO-4-(3-CHLOROPHENOXY)ANILINE synthesis

3synthesis methods
-

Yield: 100%

Reaction Conditions:

Stage #1:2-chloro-1-(3-chlorophenoxy)-4-nitrobenzene with iron;acetic acid in ethanol;water at 80; for 0.5 h;
Stage #2: with sodium hydrogencarbonate in water; pH=> 7

Steps:

4
According to Scheme 3 Step 2: A suspension of iron (5.07 mmol, 283 mg), acetic acid (1.22 mmol, 70 μL) and of 2-chloro-l-(3-chlorophenoxy)-4-nitrobenzene (1.02 mmol, 288 mg) in water/EtOH (1 :1, 8 mL) was stirred at 800C for 30 minutes. After evaporation of EtOH, the aqueous phase was basified with a saturated solution of NaHCOs and was extracted with AcOEt. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure to yield 3- chloro-4-(3-chlorophenoxy)aniline (1.02 mmol, 258 mg, 100%) as a solid. The product was used without further purification.LC (Zorbax SB-Ci8, 3.5μm, 4.6x30mm Column): RT = 2.77 min; MS m/z ES+= 254.

References:

Addex Pharma S.A. WO2009/10454, 2009, A2 Location in patent:Page/Page column 33