Sulfuric Acid → HCID 73794511, compound

A solution of 14.1 g. of o-fluoronitrobenzene in 175 ml. of ethanol and 25 ml. of dimethyl sulfoxide was hydrogenated using 350 mg. of platinum oxide until two equivalents of hydrogen were taken up. The solution of o-fluorophenylhydroxylamine was poured into a solution of 32.5 g. of ferric chloride in 500 ml. of water containing 18 ml. of sulfuric acid at 0°C. After being stirred for 30 minutes, the mixture was shaken with ether and the water was separated. The etheral solution was dried and concentrated to give 10.0 g. of crude o-fluoronitrosobenzene. This was dissolved in 250 ml. of ethyl acetate, cooled to 0°C., and 35.0 g. of mercuric oxide was added. Then 4.8 g. of dimethylhydrazine in 50 ml. of ethyl acetate was added in a dropwise fashion. The mixture was stirred 16 hours at 25°C. and was then filtered through infusorial earth. The filtrate was concentrated and chromatographed on 300 ml of silica in benzene. The product was eluted with ethyl acetate in benzene. One and seven tenths grams of 3,3-dimethyl-1-(o-fluorophenyl)triazene-1-oxide was obtained as a brown oil which gave a satisfactory n.m.r. spectrum.

1. customat 0°C
2. customthe water was separated
3. customThe etheral solution was dried
4. concentrationconcentrated
5. customto give 10.0 g
6. dissolutionThis was dissolved in 250 ml
7. stirringThe mixture was stirred 16 hours at 25°C.
8. filtrationwas then filtered through infusorial earth
9. concentrationThe filtrate was concentrated
10. customchromatographed on 300 ml of silica in benzene
11. washThe product was eluted with ethyl acetate in benzene

ORD record

ord-f1590bef81d44cf781d1a9256aa9bdc8

Source dataset

uspto-grants-1976_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03989680