2-Fluorobenzenesulphonyl chloride → 2-Fluorobenzene-1-sulfonyl fluoride

Temperature

-5 °C

A 100-L round bottomed flask fitted with overhead stirrer, nitrogen inlet, temperature probe and ice bath was charged with 2-fluorobenzenesulfonyl chloride (50 g) and tetrahydrofuran (220 g). The solution was cooled down to −5° C. with an ice bath. Tetrabutylammonium fluoride (270 mL of 1M in tetrahydrofuran solution) was added slowly to the reactor. The internal temperature was kept less than 8° C. After the addition was completed, HPLC showed the reaction was completed. The reaction was quenched by slowly adding 250 g of water. Then 430 g of toluene was added to the reaction mixture. The layers were separated. The organic layer was washed with 250 g of water twice. The organic layer was distilled down under vacuum with the bath temperature at 48° C. 1H NMR (400 MHz, CDCl3) δ 8.01-7.96 (m, 1H), 7.76-7.83 (m, 1H), 7.32-7.44 (m, 2H).

1. customA 100-L round bottomed flask fitted with overhead stirrer, nitrogen inlet
2. customwas kept less than 8° C
3. additionAfter the addition
4. customThe reaction was quenched
5. additionby slowly adding 250 g of water
6. additionThen 430 g of toluene was added to the reaction mixture
7. customThe layers were separated
8. washThe organic layer was washed with 250 g of water twice
9. distillationThe organic layer was distilled down under vacuum with the bath temperature at 48° C

ORD record

ord-3ad75118c68f4756bb4ffc9874fdd705

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08168784B2