ChemicalBook CAS DataBase List 2,6-Dimethylfluorobenzene

2,6-Dimethylfluorobenzene synthesis

12synthesis methods

Product Name:2,6-Dimethylfluorobenzene
CAS Number:443-88-9
Molecular formula:C8H9F
Molecular Weight:124.16

87-62-7
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$10.00/5 g

443-88-9
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$10.00/5g

Yield:443-88-9 86.3%

Reaction Conditions:

with sodium nitrite in Et₃N-3HF;diethyl ether

Steps:

2 Diazotization of 2,6-dimethylaniline in Et3N-3HF
EXAMPLE 2 Diazotization of 2,6-dimethylaniline in Et₃N-3HF The diazotization of 2,6-dimethylaniline (2.3 g, 0.02 mol) was performed under the same conditions as described for 2,4,6-trimethylaniline in Example 1. The reaction mixture turned yellow during the initial addition of sodium nitrite (2.0 g, 0.03 mol) and gradually turned red with the increased addition of sodium nitrite. Some tar was formed which was easily extracted with solvent. The work-up was identical to that described for 2,4,6-trimethylaniline. Diethyl ether (150 cm³) was used for the extraction of the organic layer from the aqueous washings. The organic extract was dried over magnesium sulphate. Fractional distillation of the solvent formed an orange oil which was distilled at 141-143° C. ã atmospheric pressure affording 1-fluoro-2,6-dimethylbenzene (2.0 g, 86.3%) as a colourless liquid. The distillation was complete in 1 hour. The ¹H n.m.r. spectrum contained signals at δ_H (CDCl₃) 2.25, 2-CH₃ and 6-CH₃ (d, J=2.0 Hz, 6H); 6.91, 3-H and 5-H (dd, J=8.3 Hz and J=6.5 Hz. 2H) and 7.01, 4-H (t, J=8.0 Hz, 1H). The ¹⁹F n.m.r. spectrum had a signal at δ_F (CDCl₃) 122.5, 1-F (ts, J=6.5 Hz and J=2.0 Hz). The mass spectrum produced a molecular ion at m/z 124 and the expected fragmentation pattern for 1-fluoro-2,6-dimethylbenzene at m/z 109, 103, 96, 89, 83 and 77.

References:

Rhodia Limited US6179970, 2001, B2

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