2,3-DIHYDRO-5-FLUORO-1H-INDENE-1-CARBONITRILE synthesis
- Product Name:2,3-DIHYDRO-5-FLUORO-1H-INDENE-1-CARBONITRILE
- CAS Number:915030-25-0
- Molecular formula:C10H8FN
- Molecular Weight:161.18
Yield:915030-25-0 43%
Reaction Conditions:
in N,N-dimethyl-formamide at 70; for 21 h;
Steps:
48
A solution of 1 -chloro-5-fluoroindane (1.9 g, 11.1 mmol) in 50 mL of DMF was treated with sodium cyanide (870 mg, 17.76 mmol), and the resulting reaction mixture was heated to 70 0C and stirred for 21 h. An additional portion of sodium cyanide (500 mg) was added after the first 8 h. After cooling to room temperature, the reaction mixture was poured into ice water (200 mL), and the resulting mixture was extracted with CH2Cl2 (3 x 60 mL). The combined CH2Cl2 extracts were washed with brine (60 mL), dried (Na2SO4), filtered, and evaporated to give a black liquid. Purification by column chromatography (gradient from hexane to 20% ethyl acetate/hexane) afforded the title compound as yellow-brown oil (780 mg, 43 %). 1H NMR (400 MHz, CDCl3) δ 7.37 (IH, m), 6.96 (2H, m), 4.10 (IH, m), 3.10 (IH, m), 2.95 (IH, m), 2.60 (IH, m), 2.41 (IH, m).
References:
WO2006/122200,2006,A1 Location in patent:Page/Page column 49
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