4-Bromothiophenol → 1-Bromo-4-[(2,2-diethoxyethyl)sulfanyl]benzene

Temperature

55 °C

1-Bromo-4-[(2,2-diethoxyethyl)thio]benzene (Chemical Abstracts number 96804-05-6) was prepared as described in Banfield et al.; J. Chem. Soc.; 1956; 2603-2607, and in Amin, et al.; J. Chem. Soc. Perkin Trans. 2; 1982; 1489-1492. 4-Bromothiophenol (20 g, 95%) in ethanol (80 mL) was treated with 21 wt % of sodium ethoxide in ethanol (36 g, 1.05 eq). The solution was heated at 55° C. for 30 minutes and bromoacetaldehyde diethylacetal (22.56 g, 1.05 eq) was added. The mixture was heated at reflux for 10 hours, ethanol was removed and the residue was diluted with 80 mL of water. The product was extracted with 2×120 mL of ethyl acetate. The combined ethyl acetate layer was washed with 2×40 mL of 15% NaCl and concentrated under vacuum to a brown oil (32.0 g, 92.5% potency, 96.5% yield). The product can be further purified by column chromatography (silica gel, 5:95 EtOAc:hexane).

1. temperatureThe mixture was heated
2. temperatureat reflux for 10 hours
3. customethanol was removed
4. additionthe residue was diluted with 80 mL of water
5. extractionThe product was extracted with 2×120 mL of ethyl acetate
6. washThe combined ethyl acetate layer was washed with 2×40 mL of 15% NaCl
7. concentrationconcentrated under vacuum to a brown oil (32.0 g, 92.5% potency, 96.5% yield)
8. customThe product can be further purified by column chromatography (silica gel, 5:95 EtOAc:hexane)

ORD record

ord-97329ab2631e41db9c9c1adc9e0dc323

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06969730B2