[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([SH:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[O-]CC.[Na+].[Na].Br[CH2:23][CH2:24][Cl:25]>C(O)C.C1(C)C=CC=CC=1>[Cl:25][CH2:24][CH2:23][S:16][CH:6]1[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH2:9][CH2:10][C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2
A solution of the above crude thiol (4.53 g, 0.020 mol) in absolute ethanol (7 ml) was added dropwise to a stirred solution of sodium ethoxide, freshly prepared from absolute ethanol (25 ml) and sodium (0.46 g, 0.020 mol). Stirring was continued for 0.5 h at ambient temperature. 1-Bromo-2-chloroethane (8.60 g, 0.060 mol) was added dropwise and the reaction mixture was stirred at ambient temperature for 16 h. The mixture was diluted with toluene (20 ml) and filtered. The filtrate was evaporated in vacuo and stripped with toluene, affording 5.72 g (99%) of crude 5-(2-chloroethylsulfanyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as an oil.
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