Hydrogen Bromide → 1-Bromotridecan-2-one

Temperature

0 °C

To a solution of lauric acid chloride (10.0 g, 45.7 mmol) in anhydrous THF (91 mL) at 0° C. was added dropwise a solution of trimethylsilyldiazomethane (2 M in ether, 45.7 mL, 91.4 mmol). The mixture was stirred 1 h at 0° C. then overnight at RT. The solvents were evaporated under vacuum to give a yellow oil. This crude product was dissolved in DCM (50 mL) and stirred in the presence of the PL-AMS-Resin (Polymer Laboratories, 1.54 mmol/g, 5 g) for 5 h at RT. The resin was filtered off and washed with DCM. The combined filtrates were evaporated to give a yellow oil. This crude product was dissolved in Et2O, chilled at 0° C. and a concentrated aqueous solution of HBr (48%, 10 mL) was added dropwise carefully. After 1 h of reaction, the mixture was decanted and the organic layer was dried over MgSO4, filtered and evaporated to give the title product as a beige solid (8.32 g, 66%). 1H NMR (CDCl3, 300 MHz) δ 3.87 (s, 2H), 2.63 (t, 2H, J=7.5 Hz), 1.67-1.54 (m, 2H), 1.30-1.21 (m, 16H), 0.87 (m, 3H)

1. customovernight
2. customat RT
3. customThe solvents were evaporated under vacuum
4. customto give a yellow oil
5. stirringstirred in the presence of the PL-AMS-Resin (Polymer Laboratories, 1.54 mmol/g, 5 g) for 5 h at RT
6. filtrationThe resin was filtered off
7. washwashed with DCM
8. customThe combined filtrates were evaporated
9. customto give a yellow oil
10. temperaturechilled at 0° C.
11. customAfter 1 h of reaction
12. customthe mixture was decanted
13. dry with materialthe organic layer was dried over MgSO4
14. filtrationfiltered
15. customevaporated

ORD record

ord-b9b3900e2b2844098ba3e7d0da217f4f

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592477B2