Dimethylformamide → 4-(4-methylphenoxy)benzenesulfonyl Chloride

Temperature

40 °C

To a solution of 1.84 g (10.0 mmol) of 4-methyldiphenyl ether (J. Chem. Soc., Perkin Trans. 1; 1992, 407-408) with 2 mL of dichloromethane in an ice-bath was added a solution of chlorosulfonic acid (0.73 mL, 11.0 mmol) in 2 mL of dichloromethane dropwise. The resulting mixture was stirred at 0° C. to room temperature for 2 hours, and then oxalyl chloride (11.14 mL, 13.0 mmol) was added dropwise, followed by 0.15 mL of DMF. The resulting mixture was heated to 40° C. for 1 hour and then allowed to cool to room tempereature over a 2 hour period. The reaction mixture was poured into ice-pH 7 phosphate buffer (50 mL), then extracted with EtOAc:Hexane (4:3) (3×150 mL). The combined organic layers were washed with brine (75 mL). The aqueous layer was extracted with EtOAc/Hexane(4:3) (150 mL). The organic layer was dried over Na2SO4, then evaporated by vacuum to give crude product as white solid. This solid was triturated with hexane and collected by filtration, then dried under high vacuum to give 1.555 g (57%) of 4-(4-methylphenoxy)benzenesulfonyl chloride as white solid: mp 295-300° C.; 1H--NMR (DMSO-d6) δ 2.34 (s, 3H), 6.91-6.99 (dd, J=7.7,8.4 Hz, 4H), 7.24-7.27 (d, J=8.4 Hz, 2H), 7.61-7.63 (d, J=8.1 Hz, 2H).

1. temperatureto cool to room tempereature over a 2 hour period
2. extractionextracted with EtOAc:Hexane (4:3) (3×150 mL)
3. washThe combined organic layers were washed with brine (75 mL)
4. extractionThe aqueous layer was extracted with EtOAc/Hexane(4:3) (150 mL)
5. dry with materialThe organic layer was dried over Na2SO4
6. customevaporated by vacuum
7. customto give crude product as white solid
8. customThis solid was triturated with hexane
9. filtrationcollected by filtration
10. customdried under high vacuum

ORD record

ord-734b5ce23f0e480dbe79271393f5bb6b

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05985900