Reaction SMILES: CC(C)(C)C#C/C=C/CN([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=1)C.CC(C)(C)C#C/C=C\CN(CC1C=CC=C(OC2C=CC=CC=2)C=1)C.O(C1C=C(C)C=CC=1)C1C=CC=CC=1.[Br:65]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[O:17]([C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[CH2:10][Br:65])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
Reactant: O=C1CCC(=O)N1Br
Reactant: CN(C/C=C/C#CC(C)(C)C)Cc1cccc(Oc2ccccc2)c1
Agent: CN(C/C=C\C#CC(C)(C)C)Cc1cccc(Oc2ccccc2)c1
Agent: Cc1cccc(Oc2ccccc2)c1
Agent: O=C(OOC(=O)c1ccccc1)c1ccccc1
Solvent: ClC(Cl)(Cl)Cl
Product: BrCc1cccc(Oc2ccccc2)c1

Procedure:
Following the process to be described below, Compound 2 and Compound 3 were prepared. Namely, 10.16 g of m-phenoxytoluene, 9.82 g of N-bromosuccinimide and 0.15 g of benzoyl peroxide were weighed and added to 90 ml of carbon tetrachloride as a solvent. The resulting mixture was heated under reflux for 3 hours to conduct a reaction. The reaction mixture was allowed to cool down, the insoluble matter was filtered off, and the filtrate was then concentrated. The concentrate was purified by chromatography on a silica gel column (eluent: chloroform), whereby 10.9 g of 3-phenoxybenzyl bromide were obtained. In 20 ml of methanol, 9.91 g of the reaction product were dissolved. The resulting solution was added dropwise under stirring to an ice-cooled 40% solution of methylamine in methanol, followed by stirring for 15 minutes under ice cooling. The temperature of the reaction mixture was allowed to rise to room temperature, at which the reaction mixture was stirred further for 42 hours. After the solvent was distilled off, 1 N dilute hydrochloric acid was added and the resulting mixture was washed with diethyl ether. A water layer was alkalinized with a 3 N aqueous solution of sodium hydroxide and was then extracted with diethyl ether. The thus-obtained diethyl ether solution was dried over magnesium sulfate and the solvent was distilled off. The residue was purified by chromatography on a silica gel column (eluent:chloroform:methanol=50:1), whereby 4.34 g of N-(3-phenoxybenzyl)methylamine were obtained. The reaction product was dissolved in 20 ml of N,N-dimethylformamide, to which 2.16 g of sodium carbonate were added. Under ice cooling, a solution of 4.0 g of 1-bromo-6,6-dimethyl-2-hepten-4-yne in 5 ml of N,N-dimethylformamide was added dropwise. The temperature of the resulting mixture was allowed to rise to room temperature, at which a reaction was allowed to proceed for 18 hours. After the reaction mixture was concentrated under reduced pressure, diethyl ether and water were added to conduct liquid-liquid extraction. An organic layer was collected and then washed with water and a saturated aqueous solution of sodium chloride. The extract was dried over anhydrous magnesium sulfate and concentrated, and the concentrate was purified by chromatography on a silica gel column (eluent:hexane:ethyl acetate=10:1). Relevant fractions were concentrated, whereby 2.92 g of trans-N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl-3-phenoxybenzylamine (Compound 2) and 1.08 g of cis-N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl-3-phenoxybenzylamine (Compound 3) were obtained, respectively (yields: 44.1% and 16.3%). The followings are their NMR data (CDCl3 δ ppm):