Sulfuric Acid → 8-Bromo-6-(propan-2-yl)quinoline

Temperature

100 °C

2-Bromo-4-isopropylaniline (3.0 gm) [obtained from Aldrich Chemical Co.], glycerol (2.8 mL) and arsenic pentoxide (3.22 g) were combined and heated to 100° C. H2SO4 (concentrated, 1.9 mL) was added to the reaction mixture in a dropwise manner. The mixture was then heated to 150° C. for 2.5 hours. The resulting black oil was added in a dropwise manner to a stirring mixture of saturated NaHCO3 (300 mL) and ethyl acetate (100 mL). After completion of the addition, the reaction mixture was stirred for 30 minutes. The reaction mixture was then extracted with ethyl acetate (2×200 mL). The organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The resulting material was further purified and isolated by chromatography on silica gel (30:70 ethyl acetate/hexanes) which yielded 2.5 g of 8-bromo-6-isopropylquinoline as a brown oil.

1. temperatureThe mixture was then heated to 150° C. for 2.5 hours
2. additionAfter completion of the addition
3. extractionThe reaction mixture was then extracted with ethyl acetate (2×200 mL)
4. washThe organic layers were washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe resulting material was further purified
9. customisolated by chromatography on silica gel (30:70 ethyl acetate/hexanes) which

ORD record

ord-4422fb2253a0400a84e57ee6f0de5b01

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05455252