Diethyl Ether → HCID 57443521, compound

A solution of ethyl 4-bromobenzoate (1.6 mL, 10 mmol) in anhyd THF (50 mL) was chilled to 0° C. and then charged dropwise with a 3.0 M solution of ethylmagnesium bromide in Et2O (7.0 mL, 21 mmol). After 15 min, the reaction mixture was removed from the ice-bath and stirred at ambient temperature. After 18 h the opaque mixture was quenched with satd ammonium chloride (50 mL) and extracted with Et2O (2×50 mL). The combined extracts were washed with brine, dried (anhyd Na2SO4) and concentrated under reduced pressure to give 3-(4-bromophenyl)-pentan-3-ol (2.45 g, quant) as a colorless liquid, which was used without purification in the next step: 1H-NMR (CDCl3) δ 7.46 (2H, d, J=8.3), 7.26 (2.3H, d, J=8.3), 1.78-1.86 (4H, overlapping quartets, J=7), 0.76 (6H, t, J=7.3).

1. customthe reaction mixture was removed from the ice-bath
2. customAfter 18 h the opaque mixture was quenched with satd ammonium chloride (50 mL)
3. extractionextracted with Et2O (2×50 mL)
4. washThe combined extracts were washed with brine
5. dry with materialdried (anhyd Na2SO4)
6. concentrationconcentrated under reduced pressure

ORD record

ord-d4fc6c06ddbf4eef95afc69037754b35

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863298B2