Sulfuric Acid → 2,6-Dibromobenzaldehyde

Temperature

0 °C

To anhydrous THF (70 ml), diisopropylamine (8.3 ml, 59.34 mmol) was added and then n-BuLi (1.6 M, 59.34 mmol) was slowly added dropwise at 0° C. using a syringe in a nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 30 min, and the temperature thereof was cooled to −78° C. Subsequently, 1,3-dibromobenzene (7 g, 29.67 mmol) in THF (35 ml) was slowly added using a dropping funnel. The reaction mixture was stirred at −78° C. for 30 min, following the slow addition of DMF (4.6 ml, 59.34 mmol), and then continuously stirred for 1 hour. After the termination of the reaction, an aqueous solution of dilute H2SO4 was added, and the resulting solution was extracted two times with ethyl acetate, washed with a saturated NaCl solution, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=40:1), thus obtaining the title compound as a white solid (6.64 g, 25.16 mmol, 85%).

1. temperaturethe temperature thereof was cooled to −78° C
2. stirringThe reaction mixture was stirred at −78° C. for 30 min
3. stirringcontinuously stirred for 1 hour
4. customAfter the termination of the reaction
5. extractionthe resulting solution was extracted two times with ethyl acetate
6. washwashed with a saturated NaCl solution
7. dry with materialdried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure
10. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=40:1)

ORD record

ord-162223990d7243efa680df067174ebbe

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143307B2