1-Bromo-4-fluorobenzene → HCID 70654611, compound

Temperature

100 °C

To a 0° C. slurry of NaH (460 mg, 11.4 mmol, 60 wt % dispersion in mineral oil) in DMF (14 mL) was added 1-cyclopropylethanol (0.79 mL, 7.41 mmol) dropwise. The cold bath was removed for 30 min before the addition of 1-bromo-4-fluorobenzene (1.00 g, 5.7 mmol). The resulting reaction mixture was heated to 100° C. for 3 h. At completion, the reaction was cooled to room temperature and concentrated. The resulting oil was diluted with water (30 mL) and extracted into EtOAc (3×30 mL). The combined organics were washed with brine (20 mL), then dried over MgSO4 and concentrated to provide 1-bromo-4-(1-cyclopropylethoxy)benzene (1.30 g, 95% yield). The resulting oil was used directly without further purification.

1. customThe resulting reaction mixture
2. temperatureAt completion, the reaction was cooled to room temperature
3. concentrationconcentrated
4. additionThe resulting oil was diluted with water (30 mL)
5. extractionextracted into EtOAc (3×30 mL)
6. washThe combined organics were washed with brine (20 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated

ORD record

ord-2ea3ea63f07048c3ae304cc600ca2207

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08440652B2