ChemicalBook CAS DataBase List 7-Fluoro-1-indanone

7-Fluoro-1-indanone synthesis

11synthesis methods

Product Name:7-Fluoro-1-indanone
CAS Number:651735-59-0
Molecular formula:C9H7FO
Molecular Weight:150.15

3-CHLORO-1-(2-FLUOROPHENYL)-1-OXOPROPANE

898767-04-9
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$31.00/100mg

651735-59-0
148 suppliers
$12.00/100mg

Yield:651735-59-0 32%

Reaction Conditions:

with aluminum (III) chloride;sodium chloride at 130 - 180; for 2 h;

Steps:

General Procedure E for the Synthesis of Fluoroethyl Substituted Indan Ureas A mixture of SOCl₂(1.5 eq) and substituted benzoic acids in benzene was refluxed until no more gas evolution was observed. After cooling to room temperature the mixture was concentrated on a rotary evaporator. The concentrate was taken up in dichloroethane and added to a solution of AlCl₃(1.0 eq) in dichloroethane at 10-20° C. Ethylene was bubbled for 4 hours after which the resulting mixture was stirred overnight and quenched into 4 N HCl. The resulting layers were separated and the aqueous layer was extracted with Et₂O (3×250 mL). The combined organic extracts were washed with H₂O (3×150 mL), saturated NaHCO₃(3×150 mL), brine (1×150 mL), dried over MgSO₄and concentrated. The concentrate was added to a slurry of AlCl₃(9.0 g, 10 eq) and NaCl (2.4 g, 6 eq) at 130° C. The resulting mixture was stirred at 180° C. for 2 hours. Alternatively, this concentrate was mixed with concentrated sulfuric acid and the resulting mixture was stirred at 85° C. one hour. The reaction mixture was cooled to room temperature and ice was slowly added, followed by concentrated HCl. The resulting mixture was extracted with CH₂Cl₂(3×500 mL) and the combined organic extracts were concentrated and purified by column chromatography using hexane:EtOAc (4:1) as eluant to give the desired substituted indanones^xix. Thus, the title fluoroethyl ureas were obtained from these indanones according the protocol described in general procedure C.Synthesis of 1-(2-fluoro-ethyl)-3-(7-fluoro-indan-1-yl)-ureaThe title compound was generated from commercially available 2-fluororobenzoic acid according to the general procedure E described above. The intermediates 7-fluoro-1-indanone and 7-fluoro-indan-1-ylamine were isolated and characterized.7-Fluoro-1-indanone: 6.85 g (32%) of the title indanone was obtained from 2-fluoro-benzoic acid (20.00 g, 0.14 mol), SOCl₂(15.60 mL, 0.21 mol), AlCl₃(19.00 g, 0.14 mol), an additional AlCl₃(285.50 g, 2.14 mol) and NaCl (75.10 g, 1.29 mol) according to the protocols as outlined in general procedure E above. Spectroscopic data: ¹H NMR (300 MHz, CDCl₃) δ 2.67-2.80 (m, 2H), 3.2 (t, 2H, J=5.9 Hz), 7.0 (t, 1H, J=8.5 Hz), 7.3 (d, 1H, J=7.6 Hz), 7.6 (m, 1H).