Methyl iodide → 4-Bromo-2-ethylbenzoic acid

Temperature

0 °C

To a 0° C. solution of LDA (10.7 mL, 21.39 mmol) in THF (20 mL) was added 4-bromo-2-methylbenzoic acid (2 g, 9.3 mmol) in THF (5 mL). The mixture was stirred at 0° C. for 1 h, cooled to −70° C., and then MeI (2.3 mL, 37.20 mmol) was added dropwise. The mixture was allowed to warm up to 0° C., stirred for 3 h, then quenched with H2O, and the pH was adjusted to 1-2 with 3 N HCl. The mixture was then diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by normal phase silica gel column provided 4-bromo-2-ethylbenzoic acid as a white solid.

1. temperaturecooled to −70° C.
2. temperatureto warm up to 0° C.
3. stirringstirred for 3 h
4. customquenched with H2O
5. additionThe mixture was then diluted with water
6. extractionextracted with ethyl acetate
7. washThe combined organic layer was washed with brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated in vacuo
10. customPurification by normal phase silica gel column

ORD record

ord-affe056a671e43c48e64034e4d26e834

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199994B2