Boron tribromide → 4-Bromo-2-methyl-quinolin-8-ol

BBr3 (1 M in DCM, 108 mL, 108 mmol) was added dropwise to a stirred solution of 4-bromo-8-methoxy-2-methyl-quinoline (7.8 g, 31 mmol) and triisopropyl-silane (6.2 mL, 31 mmol) in anhydrous DCM (300 mL) at −80° C. The reaction mixture was allowed to warm to room temperature over 4 h. The reaction mixture was then concentrated in vacuo and the residue was partitioned between DCM (300 mL), water (50 mL), and concentrated aqueous NH3 (20 mL). The aqueous layer was extracted with DCM (2×300 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with DCM/EA 10:1) to give the title compound. MS (m/z): 238.3 [M+H+].

1. concentrationThe reaction mixture was then concentrated in vacuo
2. customthe residue was partitioned between DCM (300 mL), water (50 mL), and concentrated aqueous NH3 (20 mL)
3. extractionThe aqueous layer was extracted with DCM (2×300 mL)
4. dry with materialThe combined organic layers were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography on silica gel (elution with DCM/EA 10:1)

ORD record

ord-aef0d4574c224ac2aea9ee9ee1df8a22

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410134B2