Methyl phenyl sulfone → Benzenesulfonamide

A solution of (phenylsulfonyl)methane (10 mmol) in 5 mL of THF at 0° C. was treated with 4.5 mL (12.6 mmol) of methylmagnesium chloride (2.8M in THF), and the resulting solution was stirred at room temperature for 30 minutes. The solution was cooled to 0° C., treated with 15 mL (15 mmol) of tributylborane (1M in THF), stirred at room temperature for 30 minutes, and then stirred at reflux for 18 hours. To the resulting mixture at 0° C. was added 5.7 g of sodium acetate, 25 mL of water, and 3.95 g of hydroxylamine-O-sulfonic acid; the resulting mixture was stirred at room temperature for 3 hours. The organic layer was diluted with ethyl acetate, washed with saturated NaHCO3 and then brine, dried (MgSO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography gave 1.06 g (67%) of phenylsulfonamide.

1. temperatureThe solution was cooled to 0° C.
2. stirringstirred at room temperature for 30 minutes
3. stirringstirred
4. temperatureat reflux for 18 hours
5. stirringthe resulting mixture was stirred at room temperature for 3 hours
6. washwashed with saturated NaHCO3
7. dry with materialbrine, dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customPurification by silica gel chromatography

ORD record

ord-e8e8f75fec534bf9aa66f53c9d27785f

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05684195