Br[CH:2]1[C:12](=[O:13])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3]1.[C-:14]#[N:15].[Na+].O.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>C1(C)C=CC=CC=1>[C:14]([CH:2]1[C:12](=[O:13])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3]1)#[N:15]2-cyanobenzocycloheptan-1-one (compound Ia) was prepared by dissolving 2-bromobenzocycloheptan-1-one (30.2 g, 0.126 mol) in toluene (150 mL) in a 500 mL round bottom flask equipped with a condenser. NaCN (18.6g, 0.38 mol), water (50 g), and dibenzo-18-crown-6 (0.5 g) were added to the flask. The reaction mixture was stirred vigorously at 90° C. under a static blanket of nitrogen for 15 hours. The reaction mixture was cooled and washed three times with water (70 mL×2+100 mL). The toluene solution was dried over sodium sulfate and filtered. The solvent was evaporated under reduced pressure. The residue was distilled under vacuum to give a yellow liquid (21.1 g, b.p. 158-162° C. at 17 mm Hg). The purity of the liquid was 96% by GC.
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