1-Bromo-3-(2,2-diethoxyethylsulfanyl)benzene synthesis

Yield: 100%

Reaction Conditions:

with potassium hydroxide in water;dimethyl sulfoxide at 20; for 120 h;

Steps:

17.1
To a stirred solution of 3-bromothiophenol (5,0 g, 26 mraol) in DMSO (40 mL) was added a solution of KOH pellets (85% by wt, 2.15 g, 32 mmol) in water (4 inL) followed by bromoacetaldehyde diethyl acetal (4.5 mL, 29 mmol). The mixture was stirred at rt for 5 d, diluted with ether (300 mL) and washed with water (3 x 100 mL). The combined water washes were extracted with ether (100 mL). The combined ether extracts were washed with brine (100 mL), dried over MgSO₄ and concentrated to afford (3-bromophenyl)(2,2-diethoxyethyl)sulfane (8.23 g, 100%) as a colorless oil.

References:

VITAE PHARMACEUTICALS, INC. WO2007/117560, 2007, A2 Location in patent:Page/Page column 145