Benzenesulfonyl chloride → HCID 10924734, compound

4-Mercaptophenol (1) (37.85 g, 300 mmol) and propargyl bromide (42.82 g, 360 mmol) were dissolved in ethyl acetate (757 ml). To the solution was added dropwise triethylamine (42.5 g, 420 mmol) over 25 minutes with stirring and under ice-cooling. After stirring for another 1.5 hours at the same temperature, triethylamine (42.5 g, 420 mmol) was added in one portion, and benzenesulfonyl chloride (63.58 g, 360 mmol) was added dropwise over 20 minutes. After keeping 1 hour at the same temperature, the cooling bath was removed and the mixture was stirred for 30 minutes at room temperature and partitioned into two layers by adding ice-water (500 ml) and 2N hydrochloric acid (110 ml). The aqueous layer was extracted with ethyl acetate (200 ml). The combined organic layer was washed with water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to provide 100.04 g of the title compound (2) as oil. Crude yield: 109%.

1. temperaturecooling
2. additionwas added dropwise over 20 minutes
3. customthe cooling bath was removed
4. stirringthe mixture was stirred for 30 minutes at room temperature
5. custompartitioned into two layers
6. additionby adding ice-water (500 ml) and 2N hydrochloric acid (110 ml)
7. extractionThe aqueous layer was extracted with ethyl acetate (200 ml)
8. washThe combined organic layer was washed with water
9. dry with materialdried over anhydrous magnesium sulfate
10. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-553d04d06f4d46e8bc56ba7f33693bf3

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06320060B1