1-Bromo-4-phenylbutane → HCID 86699932, compound

Temperature

0 °C

Under argon atmosphere at −45° C., to a stirred mixture of Lithium in pellets (0.129 g, 18.7 mmol) suspended in dry Et2O (15 mL), 4-bromo-butylbenzene (1.5 g, 7.03 mmol) in dry Et2O (10 mL), was added dropwise. The reaction was left to stir at 0° C. for 3 h, then the mixture was transferred via a cannula to a solution of 3-oxetanone (0.4 g, 5.55 mmol) in dry THF (10 mL), previously cooled to −78° C. After 3 h at −78° C., the reaction mixture was quenched with a saturated NH4Cl solution, the organic solvents removed under reduced pressure. The crude mixture was then dissolved in CH2Cl2, dried over Na2SO4, concentrated to dryness and subjected to column chromatography using a Teledyne ISCO apparatus, eluting with Cy/TBME (from 100:0 to 70:30) to afford a pure compound (0.4 g, 35%) as colorless oil. 1H NMR (CDCl3): δ 1.41-1.55 (m, 2H), 1.65-1.78 (m, 2H), 1.84-1.94 (m, 2H), 2.62-2.73 (m, 2H), 4.52 (d, J=7.2 Hz, 2H), 4.58 (d, J=7.0 Hz, 2H), 7.21 (dd, J=5.4, 7.2 Hz, 3H), 7.27-7.34 (m, 2H).

1. waitThe reaction was left
2. temperaturepreviously cooled to −78° C
3. waitAfter 3 h at −78° C.
4. customthe reaction mixture was quenched with a saturated NH4Cl solution
5. customthe organic solvents removed under reduced pressure
6. dissolutionThe crude mixture was then dissolved in CH2Cl2
7. dry with materialdried over Na2SO4
8. concentrationconcentrated to dryness
9. washeluting with Cy/TBME (from 100:0 to 70:30)

ORD record

ord-ab4bde6df7684593a7416a94aba328c1

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353075B2