Hydrochloric Acid → 2-Hydroxy-3-hexylphenylboronic acid

2-(2-Hexylphenoxy)tetrahydropyran (1.162 g, 4.43 mmol) was dissolved in dry THF (20 ml) and the solution cooled to 0° C. n-Butyl lithium (1.6M in hexanes, 4.15 ml, 6.64 mmol) was added dropwise with stirring over 10 minutes. The ice-bath was removed and the reaction stirred at room temperature overnight. Triisopropoxy borane (1.43 ml, 6.2 mmol) was added and stirring continued for 24 hours. The reaction was quenched with water, acidified to pH 1 with 2N hydrochloric acid and extracted with ether (20 ml). The combined organic extracts were washed with 2N hydrochloric acid (50 ml), dried with sodium sulphate and concentrated under vacuum. The oily solid produced was dissolved in ether (30 ml) and stirred with 2N hydrochloric acid (15 ml) for 1 hour. The organic phase was separated, dried with sodium sulphate and concentrated under vacuum. The residue was triturated with cyclohexane and the solid filtered off to give the title compound (260 mg, 26%); MS 221 (M−H)−.

1. additionwas added dropwise
2. customThe ice-bath was removed
3. stirringthe reaction stirred at room temperature overnight
4. stirringstirring
5. waitcontinued for 24 hours
6. customThe reaction was quenched with water
7. extractionextracted with ether (20 ml)
8. washThe combined organic extracts were washed with 2N hydrochloric acid (50 ml)
9. dry with materialdried with sodium sulphate
10. concentrationconcentrated under vacuum
11. customThe oily solid produced
12. customThe organic phase was separated
13. dry with materialdried with sodium sulphate
14. concentrationconcentrated under vacuum
15. customThe residue was triturated with cyclohexane
16. filtrationthe solid filtered off

ORD record

ord-758c46801f7b456294c890d877601088

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06541490B1