ChemicalBook CAS DataBase List 2-Fluoro-p-Xylene

2-Fluoro-p-Xylene synthesis

6synthesis methods

Product Name:2-Fluoro-p-Xylene
CAS Number:696-01-5
Molecular formula:C8H9F
Molecular Weight:124.16

2-Fluoro-p-Xylene was prepared by Schiemann reaction of 2,5-dimethylaniline.

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Yield: 65.5%

Reaction Conditions:

with sodium nitrite in Et₃N-3HF

Steps:

3 Diazotization of 2,5-dimethylaniline in Et3N-3HF
EXAMPLE 3 Diazotization of 2,5-dimethylaniline in Et₃N-3HF 2,5-Dimethylaniline (2.3 g, 0.02 mol) was syringed into Et₃N-3HF (30 cm³) over a 35 minute period. The reaction mixture turned red during the addition of sodium nitrite (2.0 g, 0.03 mol) and a significant amount of nitrogen was evolved during the reaction. Although a high proportion of sodium nitrite was seen to dissolve a greater proportion of tarry material was formed. The mixture was poured into water (150 cm³) and the remaining contents of the flask washed with further water (30 cm³*2). The mixture was extracted with diethyl ether (150 cm³*2) and the organic layer dried over magnesium sulphate. Fractional removal of diethyl ether afforded an orange oil. Distillation of the oil at 144-146° C. ? atmospheric pressure afforded 1-fluoro-2,5-dimethylbenzene (1.52 g, 65.5%) as a clear colourless liquid. The ¹⁹F n.m.r. spectrum had a signal at δ_F (CDCl₃) 121.9, 1-F (ddq, J=8.5 Hz, J=10.5 Hz and J=2.2 Hz). From the GC/MS the compound showed the expected molecular ion at m/z 124 and the expected fragmentation for 1-fluoro-2,5-dimethylbenzene at m/z 109, 101, 96, 83 and 77.

References:

Rhodia Limited US6179970, 2001, B2