Octylbenzene → 2-Bromo-1-(4-octylphenyl)ethanone

To a flame dried round bottom flask equipped with a magnetic stirbar under an inert atmosphere was added AlCl3 (5.47 g; 41 mmol) followed by 1,2-dichloroethane (22 mL). The stirring suspension was then brought to 0° C. and 1-phenyloctane (7.99 mL, 36 mmol) was added in one portion. Bromoacetyl bromide (3.75 mL, 43 mmol) was then added dropwise over a period of 10 minutes. Upon completing addition of the acid bromide, the reaction mixture was brought to rt and stirred for 2 h. The reaction mixture was then quenched carefully by slow addition of H2O (36 mL) without ever letting the reaction mixture exceed 45° C. producing a suspension of solid white precipitate. The aqueous layer of the quenched reaction mixture was discarded and the organic phase washed once with 10% HCl (10 mL), washed once with H2O (10 mL), and dried over magnesium sulfate. The dried organic phase was then concentrated in vacuo to a green/brown oil. Recrystallization from MeOH/H2O provided the product 1 (6.36 g, 57%) as white needles in three crops. Rf=0.21 (1:19 EtOAc/hexanes).

1. customTo a flame dried round bottom flask
2. customequipped with a magnetic stirbar under an inert atmosphere
3. customwas then brought to 0° C.
4. customwas brought to rt
5. customThe reaction mixture was then quenched carefully by slow addition of H2O (36 mL)
6. customexceed 45° C.
7. customproducing
8. additiona suspension of solid white precipitate
9. customThe aqueous layer of the quenched reaction mixture
10. washthe organic phase washed once with 10% HCl (10 mL)
11. washwashed once with H2O (10 mL)
12. dry with materialdried over magnesium sulfate
13. concentrationThe dried organic phase was then concentrated in vacuo to a green/brown oil
14. customRecrystallization from MeOH/H2O

ORD record

ord-481dc7d3bf574c26a9cd7166d7ec2889

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560477B2