Reaction SMILES: Cl[CH2:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.S(=O)(=O)(O)[OH:14].Cl>>[F:11][C:8]1[CH:7]=[C:6]2[C:5](=[CH:10][CH:9]=1)[C:4](=[O:14])[CH2:3][CH2:2]2
Reactant: O=S(=O)(O)O
Reactant: O=C(CCl)Cc1ccc(F)cc1
Agent: Cl
Product: O=C1CCc2cc(F)ccc21
Temperature: 20 °C
Yield: 33 %

Procedure:
The procedure used for the preparation of 5-fluoro-1-indanone is that of Olivier and Marechal (E. Bull. Soc., Chim. Fr. (1973) 3092-3095) with modifications. The conversion of the ketone to 7-fluoro-5H-indeno[1,2-b]pyridine followed the general procedure described by Parcell and Hauck (J. Org. Chem. (1963) 28, 3468-3473) for the preparation of 5H-indeno[1,2b]pyridine from 1-indanone. ##STR110## Aluminum chloride (350 g, 2.62 mol) was covered with 650 mL methylene chloride and, while stirring under nitrogen, a solution of 3-chloropropionyl chloride (400 g, 3.15 mol, 300 mL) in 250 mL methylene chloride was added over 80 min. After 15 min., a solution of fluorobenzene (256 g, 2.66 mol, 250 mL) in 250 mL methylene chloride was added over 1 h 35 min. The reaction mixture was stirred, under nitrogen, at room temperature overnight (ca 18 h). The mixture was then poured onto 2.5 kg ice and transferred to a 4 L separatory funnel. After shaking well, the organic layer was removed and the aqueous portion was extracted with 2×50 mL methylene chloride. The combined organic extracts were washed with 3×200 mL saturated aqueous sodium bicarbonate and 1×200 mL brine, dried (MgSO4), and evaporated to leave an oil which crystallized on cooling. Recrystallization from 2L hexane gave 325 g (67%). The filtrate was concentrated to 500 mL and cooled to provide another 42 g ((9%) of product (46). ##STR111## 3-Chloro-1-(4-fluorophenyl)propanone (46) (366 g, 1.97 mol) and 2.2L concentrated sulfuric acid were combined in a 5L flask equipped with a mechanical stirrer and heated over a period of 80 min. to 120° C. and then maintained at that temperature for 30 min. Hydrogen chloride evolution began at about 80° C. The reaction mixture was then cooled to 20° C., poured onto 5 kg of ice in a 22L flask equipped with a bottom drain and a mechanical stirrer, and extracted with 6×1L chloroform. The combined extracts were washed with 2×1L saturated aqueous sodium bicarbonate and 1×1L brine, dried (MgSO4), and concentrated to leave a dark oil. Distillation gave the ketone, (47) 97.9 g (33%), bp (61°-66° C./0.15-0.2 mm, discolored by some dark material which was carried over during the process. ##STR112## A solution of 5-fluoro-1-indanone (47) (20.2 g, 0.135 mol), p-toluene-sulfonic acid monohydrate (0.015 eq, 390 mg), and piperidine (1.1 eq, 0.148 mol. 15 mL) in 300 mL toluene was refluxed under a Dean-Stark trap for 30 h. The reaction mixture was concentrated and distilled to provide the enamine, (48) 8.6 g (29%); bp 95°-100° C./1.5 mm. ##STR113## A solution of the enamine (8.6 g, 40 mmol) in 10 mL dry DMF was added all at once to a stirred solution of bromopropylamine hydrobromide (1.0 eq, 8.67 g) in 15 mL DMF. The stirred mixture was heated to 100° C. under nitrogen and then kept at that temperature for 4 h. The reaction mixture was poured into 60 mL cold 2N aqueous hydrochloric acid and extracted with 2×50 mL ethyl ether to remove any non-basic material. The aqueous solution was then covered with 50 mL ether, chilled, and basified using concentrated, sodium hydroxide. After separating the organic layer, the aqueous portion was extracted with 2×50 mL ether and the combined extracts were washed with 1×50 mL brine, dried (MgSO4), and concentrated to leave 7.8 g of a dark oil. Distillation provided the tetrahydropyridine, 3.46 g (46%); bp 83°-86° C./0.15 mm. ##STR114## A mixture of the tetrahydropyridine (49) (3.19 g, 16.9 mmol), 10 mL xylene, 10 mL nitrobenzene, and 350 mg 10% palladium on carbon was refluxed for 4 h under a Dean-Stark trap under nitrogen. The reaction mixture was then cooled to room temperature and filtered through Celite, washing with ethyl acetate. The filtrate was extracted with 3×20 mL 2N aqueous hydrochloric acid and then the combined extracts were washed with 2×25 mL ethyl ether to remove non-basic material. Basification using solid potassium carbonate resulted in the precipitation of a dark green solid that was collected by filtration and washed well with water. This material 2.3 g (75%), was judged sufficiently pure by NMR to use in the next step. The material can further be purified by chromatography on silica gel using 30% ethyl acetate/hexane to give a yellow solid of (50) mp 80°-84° C.