HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulfuric Acid → 7-bromo-2-(bromomethyl)-6-fluoro-4H-1,3-benzodioxine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | 2-Bromo-1,1-dimethoxyethane | HCID 81672 | — |
| Reactant | 5-Bromo-4-fluoro-2-(hydroxymethyl)phenol | HCID 67156027 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 7-bromo-2-(bromomethyl)-6-fluoro-4H-1,3-benzodioxine | HCID 67155779 | 45.7% |
Reaction Steps
Preparation according to Preparation 9. 5-bromo-4-fluoro-2-(hydroxymethyl)phenol (2.3 g, 10.4 mmol), 2-bromo-1,1-dimethoxyethane (9.9 ml, 83 mmol), dry THF (30 ml) and concentrated H2SO4 (4 ml) were heated at 55° C. for 2 h. Purification by flash column chromatography (isooctane/EtOAc 10:1) gave the title compound (1.55 g). MS m/z (rel. intensity, 70 eV) 328 (M+, 11), 326 (M+, 23), 324 (M+, 12) 204 (98), 202 (bp), 176 (41), 174 (43), 95 (59).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08492372B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-7e8a402645ce424bbff8b89cb5f8f6b3 |
| Source note | uspto-grants-2013_07 |