Glycerol → 6-Bromo-7-methylquinoline
Reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].O[CH2:11][CH:12]([CH2:14]O)O.[N+](C1C=CC=CC=1)([O-])=O.S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][C:3]=1[CH3:9])[N:6]=[CH:14][CH:12]=[CH:11]2Participants
Procedure
A mixture of 4-bromo-3-methylaniline (20 g, 107.5 mmol), ferric sulfate (6.6 g, 43.4 mmol), glycerol (40.8 g, 440 mmol), nitrobenzene (8.12 g, 66 mmol), and concentrated sulfuric acid (23 ml) was heated gently. After the first vigorous reaction, the mixture was boiled for 3 h and then evaporated to remove the excess nitrobenzene. The solution was added a saturated aqueous solution of sodium bicarbonate until pH=7-8, then the solution was filtered and extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The solid was purified by flash column chromatography to give a yellow solid, which was further washed with petroleum ether to give 7.5 g of 6-bromo-7-methyl-quinoline (31% yield): 1H NMR (CDCl3): 2.60 (s, 3H), 7.36 (m, 1H), 7.96 (s, 1H), 8.04 (m, 2H), 8.89 (m, 1H).
Workup
- temperaturewas heated gently
- customAfter the first vigorous reaction
- customevaporated
- customto remove the excess nitrobenzene
- additionThe solution was added a saturated aqueous solution of sodium bicarbonate until pH=7-8
- filtrationthe solution was filtered
- extractionextracted with dichloromethane
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe solid was purified by flash column chromatography
- customto give a yellow solid, which
- washwas further washed with petroleum ether
Sources & evidence
- ORD record
- ord-7ca93d444f154be68f99246e895e0e59
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507489B2
Reaction notes
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