Hydrochloric Acid → 2-Ethyl-5-bromophenylboronic acid

To a solution of 4-bromo-1-ethyl-2-iodobenzene (10.00 g, 32.20 mmol) in anhydrous tetrahydrofuran (60 ml) at −78° C. is added a solution of isopropylmagnesium chloride (16.90 ml, 33.80 mmol, 2M solution in tetrahydrofuran) dropwise, maintaining a temperature below −60° C. After stirring for 20 minutes the reaction mixture is allowed to slowly warm to room temperature followed by an additional hour of stirring. The solution is re-cooled to −78° C. and trimethylborate (7.18 ml, 64.32 mmol) is added dropwise, after which the mixture is again allowed to warm to room temperature with further stirring for 2 hours. Dilute aqueous hydrochloric acid (30 ml) is added, and the crude product is extracted into ethyl acetate (100 ml). The aqueous phase is washed with ethyl acetate (2×100 ml), and all organics are combined, dried over anhydrous magnesium sulfate then concentrated in vacuo to give a light brown solid which is triturated with hexanes to afford 5-bromo-2-ethylphenylboronic acid (6.46 g) as a cream powder.

1. temperaturemaintaining a temperature below −60° C
2. waitfollowed by an additional hour
3. stirringof stirring
4. temperatureThe solution is re-cooled to −78° C.
5. temperatureto warm to room temperature
6. stirringwith further stirring for 2 hours
7. extractionthe crude product is extracted into ethyl acetate (100 ml)
8. washThe aqueous phase is washed with ethyl acetate (2×100 ml)
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationthen concentrated in vacuo
11. customto give a light brown solid which
12. customis triturated with hexanes

ORD record

ord-e6aaaab91eab4c99b674b02d266934a8

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741806B2