Sulfuric Acid → HCID 21904677, compound

HRID 1931563Notes

Reaction equation

S(=O)(=O)(O)O.[F:6][C:7]1[CH:8]=[C:9](N)[CH:10]=[CH:11][C:12]=1[S:13][CH3:14].[O:16]1CCCC1.N([O-])=O.[Na+]>O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[Cu-]=O>[F:6][C:7]1[CH:8]=[C:9]([OH:16])[CH:10]=[CH:11][C:12]=1[S:13][CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

Concentrated sulfuric acid (40 mL) was added to a rapidly stirred mixture of 3-fluoro-4-methylsulfanyl-phenylamine (15.5 g, 99 mmol), water (750 mL) and tetrahydrofuran (23 mL). The mixture was cooled to 0° C. and a solution of sodium nitrite (7.5 g, 163 mmol) in water (15 mL) was added. The resulting mixture was stirred for 2 h at 0° C. and it was then added dropwise over 10 min to a stirring solution of copper(II) nitrate (230 g, 1.2 mol) and copper(I) oxide (12.8 g, 89 mmol) in water (1 L). The reaction mixture was stirred for 15 min and then extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (sodium sulfate), filtered, evaporated, and purified by column chromatography, eluting with 20% ethyl acetate/hexanes to give 3-fluoro-4-methylsulfanyl-phenol (3.73 g, 24%) as a brown oil.

Workup

stirringThe reaction mixture was stirred for 15 min
extractionextracted twice with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried (sodium sulfate)
filtrationfiltered
customevaporated
custompurified by column chromatography
washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-c9d39a5e9580465eb51dd4669620f19e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

Loading…