[CH2:1]([N:3]([CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:3]([CH2:11][CH2:12][O:13][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][O:14]1)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2]
14.7 g (60.3 mmols) of N-ethyl-N-(2-hydroxyethyl)-4-bromoaniline, 90 ml of chloroform, 10.68 ml (2.0-fold equivalent weight) of 3,4-dihydro-2H-pyran and 0.76 g (0.05-fold equivalent weight) of pyridine p-toluenesulfonate were mixed, and the mixture obtained was heated at 70° C. for 1.5 hours in an atmosphere of argon. Thereafter, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution obtained, which was then extracted with chloroform (200 ml×2). The organic layer thus formed was washed with a saturated aqueous sodium hydrogencarbonate solution, which was then dried with anhydrous magnesium sulfate and thereafter concentrated. The residue thus obtained was purified by silica gel column chromatography (developing system: chloroform) to obtain 18.90 g of N-ethyl-N-[2-(tetrahydropyran-2-yl)oxyethyl]-4-bromoaniline (yield: quantitative; a colorless oily liquid).
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