Water → HCID 53995284, compound

To a solution of 3,5-dichloro-4-(methylsulfonyl)benzoic acid ethyl ester (2.6 g) in tetrahydrofuran (50 mL) was added lithium triethylborohydride (1 M in tetrahydrofuran, 24 mL) at 0-5° C. under nitrogen. The mixture was stirred for 30 min and then water (2 mL) was added and the tetrahydrofuran was evaporated under vacuum. Toluene (100 mL) and water (30 mL) w ere added and then hydrogen peroxide (30% in water, 20 mL) was added at 10-20° C. After 30 min, the separated solid was dissolved by adding ethyl acetate (100 mL). The organic phase was separated and washed with saturated sodium pyrosulfite solution (25 mL) and then with potassium bicarbonate solution (1 M, 25 mL) and then dried with sodium sulphate and evaporated to dryness (yield 1.8 g). 1H-NMR (400 MHz, DMSO-d6) d=3.43 (s, 3H), 4.57 (s, 2H), 5.6 (b, 1H), 7.59 (s, 2H).

1. customthe tetrahydrofuran was evaporated under vacuum
2. additionToluene (100 mL) and water (30 mL) w ere added
3. additionhydrogen peroxide (30% in water, 20 mL) was added at 10-20° C
4. waitAfter 30 min
5. dissolutionthe separated solid was dissolved
6. additionby adding ethyl acetate (100 mL)
7. customThe organic phase was separated
8. washwashed with saturated sodium pyrosulfite solution (25 mL)
9. dry with materialwith potassium bicarbonate solution (1 M, 25 mL) and then dried with sodium sulphate
10. customevaporated to dryness (yield 1.8 g)

ORD record

ord-b651d99d34834dfa84fc81a5528db9d3

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06201027B1