2,6-Dichlorophenol → 2-(2-bromoethoxy)-1,3-dichlorobenzene

Temperature

100 °C

Into a 10 mL round bottom flask was added 2,6-dichlorophenol (326 mg, 2 mmol) and DMF (2 mL). Potassium carbonate (276 mg, 2 mmol, 10 eq) and 1,2-dibromoethane (3.76 g, 20 mmol, 10 eq) was added. The flask was fitted with a reflux condenser and nitrogen inlet and the reaction heated to 100° C. for 2 hours. The mixture was partitioned between water (20 mL) and chloroform (20 mL). The organic layer was separated and the aqueous layer was further extracted with chloroform (3×20 mL). The organic layers were combined, washed twice with 10% sodium carbonate (20 mL) and once with brine (20 mL). The combined organic phase was dried over sodium sulfate and filtered. Solvent was removed under vacuum to leave a brown oil of 2A (264 mg, 49%) which was analytically pure.

1. customThe flask was fitted with a reflux condenser and nitrogen inlet
2. customThe mixture was partitioned between water (20 mL) and chloroform (20 mL)
3. customThe organic layer was separated
4. extractionthe aqueous layer was further extracted with chloroform (3×20 mL)
5. washwashed twice with 10% sodium carbonate (20 mL) and once with brine (20 mL)
6. dry with materialThe combined organic phase was dried over sodium sulfate
7. filtrationfiltered
8. customSolvent was removed under vacuum

ORD record

ord-5d13867e5e7643e78fdb61419ccfd1b2

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129538B1