Allyl bromide → HCID 637358, compound

To a suspension of 2-chloro-5-methylphenol (10.0 g, 0.07 mol) and potassium carbonate (11.7 g, 0.08 mol) in acetonitrile (200 mL) at 82° C., was dropwise added a solution of allyl bromide (9.6 mL, 0.11 mol) in acetonitrile (50 mL). The mixture was reflux overnight. Once at room temperature, the mixture was filtered and the precipitate rinsed with diethyl ether. The filtrate was then concentrated in vacuo. The residue was dissolved in diethyl ether (250 mL) and washed with a 2N sodium hydroxide solution (150 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 1-chloro-4-methyl-2-(prop-2-en-1-yloxy)benzene (7a) (12.72 g, 0.07 mol, 99%) which was used without further purification.

1. temperatureThe mixture was reflux overnight
2. filtrationOnce at room temperature, the mixture was filtered
3. washthe precipitate rinsed with diethyl ether
4. concentrationThe filtrate was then concentrated in vacuo
5. dissolutionThe residue was dissolved in diethyl ether (250 mL)
6. washwashed with a 2N sodium hydroxide solution (150 mL)
7. dry with materialThe organic layer was dried over sodium sulfate
8. concentrationconcentrated in vacuo

ORD record

ord-b5885ab87e9d4f3c8a1301ea721c2607

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260395B2