[Br:1][C:2]1[CH:3]=C(O)C(OC)=CC=1.N12CCN(CC1)C[CH2:12]2.[CH3:19][N:20]([CH3:24])[C:21](Cl)=[S:22].[OH2:25].CN1[C:31](=[O:32])[CH2:30][CH2:29][CH2:28]1>>[CH3:19][N:20]([CH3:24])[C:21](=[S:22])[O:25][C:30]1[CH:29]=[CH:28][C:2]([Br:1])=[CH:3][C:31]=1[O:32][CH3:12]A mixture of 4-bromoguaiacol (2.05 g, 10.1 mmol) and 1,4-diazabicyclo(2.2.2)octane (1.42 g, 12.6 mmol) in NMP (24 mL) was heated at 50° C. to give a dark-yellow solution. A solution of dimethylthiocarbamoyl chloride (1.37 g, 11.1 mmol) in NMP (2 ml) was added dropwise to the previous solution over 1-2 min. Some precipitated has formed during the addition. The mixture was stirred at 50° C. for 3 h, and then water (25 ml) was added over 5 min at 50° C. The mixture was stirred overnight at r.t., and the precipitate was isolated by filtration, washed twice with water, and dried in vacuo at 50° C. to yield a pale creamed-coloured crystalline solid, 2.11 g (72%).
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