Cesium carbonate → 2-(3-BroMo-phenoxy)-ethanol

A mixture of 3-bromo-phenol (10 g, 56.64 mmol), 2-bromoethanol (4.65 mL) and cesium carbonate (18.64 g, 1 eq.) in DMF (25 mL) was stirred at rt for overnight. The mixture was then heated in a 70° C. oil bath for about 3 hours. More 2-bromoethanol (3 mL) was added and heating was increased to 80° C. and stirred for overnight. The reaction was allowed to cool to rt and the insolubles were filtered off. The filtrate was poured into water and extracted with ethyl acetate (2×200 mL), washed with 10% Na2CO3 (3×), brine (2×), dried and concentrated. The residue was purified on a silica gel column to give 2-(3-bromo-phenoxy)-ethanol.

1. temperatureThe mixture was then heated in a 70° C. oil bath for about 3 hours
2. temperatureheating
3. temperaturewas increased to 80° C.
4. stirringstirred for overnight
5. temperatureto cool to rt
6. filtrationthe insolubles were filtered off
7. additionThe filtrate was poured into water
8. extractionextracted with ethyl acetate (2×200 mL)
9. washwashed with 10% Na2CO3 (3×), brine (2×)
10. customdried
11. concentrationconcentrated
12. customThe residue was purified on a silica gel column

ORD record

ord-90ff8bf3c0984893a2895a8c861660ad

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06677368B2