Potassium Nitrate → 4-(Ethylsulfonyl)-1-fluoro-2-nitrobenzene

HRID 45407

Reaction equation

[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1)(=[O:4])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 1-(ethylsulfonyl)-4-fluorobenzene (1.36 mmol, 0.257 g) in sulfuric acid (1.32 ml) was added potassium nitrate (0.243 g) at 80° C. The mixture was stirred at 90° C. for 2 hours. Ice water (5 ml) was added and the mixture was extracted with ethyl acetate (25 ml) and washed with water (20 ml) and brine (10 ml). The organic extracts were combined and dried over sodium sulfate and concentrated. The residue was purified by column chromatography (hexane/ethylacetate 1:3) to give a light yellow solid which was crystallized from methanol. HPLC indicated 98% purity, mp 128-131° C., (0.21 g, 66% yield). 1H NMR (CDCl3): 1.35 (t, 3H, CH3), 3.21 (q, 2H, CH2), 7.55 (t, 1H, Ar—H), 8.21 (m, 1H, Ar—H), 8.64 (d, 1H, Ar—H); MS: 229 M−. Elemental Analysis (C, H, N, F, S) for C8H8FNO4S; calculated C, 41.20; H, 3.46; N, 6.01; F, 8.15; S, 13.75. found C, 41.31; H, 3.35; N, 5.85; F, 8.17; S, 13.53.

Workup

extractionthe mixture was extracted with ethyl acetate (25 ml)
washwashed with water (20 ml) and brine (10 ml)
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by column chromatography (hexane/ethylacetate 1:3)
customto give a light yellow solid which
customwas crystallized from methanol

Sources & evidence

ORD record: ord-f71feadad67f41ecaa39e431e9b6e979
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541476B2

Linked notes

Loading…