Hydrochloric Acid → 1-Chloro-4-fluoro-2-(trifluoromethyl)benzene

4-Chloro-3-(trifluoromethyl)benzenamine (19.5 g, 100 mmoles), water (40 ml) and c.hydrochloric acid (40 ml) were heated with stirring on a steam bath until a white solid formed. The mixture was cooled (ice-salt bath) and a solution of sodium nitrite (7 g, 101 mmoles) in water (15 ml) was added over 15 mins. After stirring for a further hour at 0°, tetrafluoroboric acid (30 g of 40% aqueous solution) was added dropwise over 15 minutes. After one hour the solid was filtered off, washed with water (10 ml), methanol (30 ml) and ether (30 ml) and then dried in vacuo. The dry compound was heated at 140°-180° until no more fumes were observed. The cooled residue was dissolved in ethyl acetate, washed with 5% aqueous sodium hydroxide, dried (Na2SO4) and the solvent was removed in vacuo. The residue was distilled in vacuo (12 mmHg, oven temperature 50°-55°) to give the sub-title compound as a colourless oil (7.5 g). M+ 200/198; nmr (CDCl3)δ7.8-7.2 (m).

1. customformed
2. stirringAfter stirring for a further hour at 0°
3. filtrationAfter one hour the solid was filtered off
4. washwashed with water (10 ml), methanol (30 ml) and ether (30 ml)
5. customdried in vacuo
6. temperatureThe dry compound was heated at 140°-180° until no more fumes
7. dissolutionThe cooled residue was dissolved in ethyl acetate
8. washwashed with 5% aqueous sodium hydroxide
9. dry with materialdried (Na2SO4)
10. customthe solvent was removed in vacuo
11. distillationThe residue was distilled in vacuo (12 mmHg, oven temperature 50°-55°)

ORDレコード

ord-faae922f17554e71923cbf62d3b798bf

出典データセット

uspto-grants-1987_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04686217