Hydrochloric Acid → 2-(2-Bromophenyl)propan-2-ol

Temperature

-2.5 °C

To a stirring solution of methyl 2-bromobenzoate (XCIV) (5 g, 0.0233 mol) in THF (30 mL) under argon at 0° C. was added dropwise MeMgBr (19.4 mL, 0.058 mol), maintaining the temperature in the range of −5 to 0° C. The reaction mixture was stirred at 0° C. for 1 hour and then at room temperature overnight. The mixture was cooled to 0° C. and 1M aqueous HCl (35 mL) was added, maintaining the temperature below 5° C., after which it was allowed to reach room temperature and was stirred for 30 minutes. To this mixture EtOAc (35 mL) was added and after stirring for 5 minutes a white precipitate was removed by filtration through a Celite pad. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic fractions were concentrated, washed with brine and dried over MgSO4. Crude XCV was purified by silica gel chromatography using DCM then DCM/MeOH 300/1 to give 2-(2-bromophenyl)propan-2-ol (XCV) as a light yellow oil (4.55 g; 21.2 mmol, 91% yield). 1H NMR (CDCl3) δ ppm 1.75 (s, 6H), 2.85 (brs, 1H), 7.09 (td, J=7 Hz, J=2 Hz, 1H), 7.29 (td, J=7 Hz, J=1 Hz, 1H), 7.58 (dd, J=7, J=1, 1H), 7.67 (dd J=7, J=2, 1H).

1. customat room temperature
2. customovernight
3. temperatureThe mixture was cooled to 0° C.
4. temperaturemaintaining the temperature below 5° C.
5. customto reach room temperature
6. stirringwas stirred for 30 minutes
7. stirringafter stirring for 5 minutes a white precipitate
8. customwas removed by filtration through a Celite pad
9. customThe layers were separated
10. extractionthe aqueous layer was extracted with EtOAc
11. concentrationThe combined organic fractions were concentrated
12. washwashed with brine
13. dry with materialdried over MgSO4
14. customCrude XCV was purified by silica gel chromatography

ORD record

ord-a5a0a50970d5421490d46cff6c114522

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933018B2