Thiophene → HCID 12060894, compound

To stirred solution of m-bromoaniline (34.4 g; 0.2M) in thiophene (200 mL) was added isoamylnitrite (46.86 g; 0.4M) dropwise over a period of 30 mins. at 0° C. The resulting mixture was cautiously warmed to R.T. and heated to reflux for 16 hours. The reaction mixture was cooled, diluted with 400 mL of ether, washed with 3×100 mL of satd. sodium chloride solution, and dried over anhydrous magnesium sulfate. Solvent and excess thiophene were removed. A solution of the residue in 200 mL of ether was filtered through 50 G silica gel bed. Solvent was removed, and the residue was distilled to give 34% of 2-(3'-bromophenyl)thiophene as a yellow liquid boiling at 130°-2°/~0.2 mm. This liquid solidified on standing in the refrigerator.

1. customat 0° C
2. temperatureheated
3. temperatureto reflux for 16 hours
4. temperatureThe reaction mixture was cooled
5. washwashed with 3×100 mL of satd
6. dry with materialsodium chloride solution, and dried over anhydrous magnesium sulfate
7. customSolvent and excess thiophene were removed
8. filtrationA solution of the residue in 200 mL of ether was filtered through 50 G silica gel bed
9. customSolvent was removed
10. distillationthe residue was distilled

ORD record

ord-ce1f23167bbc4e8281abd639a6e1f6cb

Source dataset

uspto-grants-1992_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05143914