HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulfuric Acid → 1-Bromo-5-fluoro-2-iodo-3-nitrobenzene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | 2-Bromo-4-fluoro-6-nitroaniline | HCID 292004 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-Bromo-5-fluoro-2-iodo-3-nitrobenzene | HCID 19429770 | 78% |
Reaction Steps
Mix 4-fluoro-2-bromo-6-nitroaniline (15.5g, 66.0mmol) and 50% sulfuric acid (200mL) and cool to 0°-5° C. Add, by dropwise addition, a solution of sodium nitrite (6.0g, 86.4mmol ) in water (50mL) Stir for 30 minutes and add solid potassium iodide (29g, 173mmol). Take up the product in ethyl acetate (300mL) wash with saturated sodium hydrogen carbonate (2×200mL), saturated sodium metabisulfite (2×200mL) and water (200mL). Dry (MgSO4), evaporate the solvent in vacuo and purify by silica gel chromatography to give 1-iodo-2-nitro-4-fluoro-6-bromobenzene as a yellow crystalline solid (17.81g, 76%); mp 75°-76° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05360814 |
| Source dataset | uspto-grants-1994_11 |
| ORD ID | ord-81fff2d4b4604e92bc9e8e853f17c40e |
| Source note | uspto-grants-1994_11 |