Bromobenzene → Benzyl 3-Bromopropyl Ether

To the Grignard reagent prepared from bromobenzene (46.3 g., 0.294 mole) and magnesium (7.15 g., 0.294 mole) in ether (150 ml.) is added, dropwise over one hour at 0°, a solution of 3-chloromethoxy-1-bromopropane (55.0 g., 0.294 mole) in ether (50 ml.). The resulting solution is stirred at 25° for 16 hours, then heated at reflux for 1/4 hour, cooled to 0° and cautiously treated with ice water (200 ml.) with vigorous stirring. After separating the phases, the aqueous layer is extracted with ether (200 ml.). The combined organic extract is washed with water, 5% potassium carbonate, water and saturated brine, dried over sodium sulfate and evaporated in vacuo leaving a pale yellow oil (64.4 g., 96%) which is distilled to provide the title compound as a colorless liquid (92% recovery), b.p. 140°-141°/14 mm.; pmr (CDCl3)δ2.12 (2H,p), 3.51 (2H,t), 3.60 (2H,t), 4.50 (2H,t) and 7.31 (5H,s).

1. additionis added, dropwise over one hour at 0°
2. temperatureheated
3. temperatureat reflux for 1/4 hour
4. temperaturecooled to 0°
5. customAfter separating the phases
6. extractionthe aqueous layer is extracted with ether (200 ml.)
7. extractionThe combined organic extract
8. washis washed with water, 5% potassium carbonate, water and saturated brine
9. dry with materialdried over sodium sulfate
10. customevaporated in vacuo
11. customleaving a pale yellow oil (64.4 g., 96%) which
12. distillationis distilled

ORD record

ord-66f3cbf622624516942fef48de87a704

Source dataset

uspto-grants-1978_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04066692