Bromine → HCID 68900274, compound

HRID 735328Notes

Reaction equation

HRID 735328 reaction equation
[Br:1]Br.Cl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][CH:17]=[N:18]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1>[N+](C1C=CC=CC=1)([O-])=O.C1(C)C=CC=CC=1>[Br:1][C:16]1[CH:17]=[N:18][C:19]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([C:8]1[CH:9]=[CH:10][C:5]([F:4])=[CH:6][CH:7]=1)[CH:20]=2

Participants

5

Reactant 2

HCID 24408BromineHCID 68899098HCID 68899098, compound

Product 1

HCID 68900274HCID 68900274, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7416NitrobenzeneSolvent2×

Conditions

Temperature
140 °C

Procedure

A solution of bromine (0.9 mL, 17.6 mmol) in nitrobenzene (2.5 mL) was added dropwise over 15 minutes to a thick slurry of 7-(4-fluorophenyl)quinoline hydrochloride (3.80 g, 14.6 mmol) in nitrobenzene (7.5 mL) at 140° C. (oil bath temperature). The resulting mixture was stirred at 140° C. for 6 hours, allowed to cool to ca. 80° C., diluted with toluene (30 mL) and then cooled to room temperature. The orange solid was collected under suction and washed with toluene followed by diethyl ether. The solid was suspended in water (100 mL), the mixture basified with aqueous sodium carbonate and extracted with dichloromethane (2×50 mL). The combined extracts were dried (MgSO4) and evaporated to give a yellow solid. This was purified by flash chromatography, eluting with 2:1 dichloromethane/isohexane, dichloromethane then 5% ethyl acetate/dichloromethane, to afford 3-bromo-7-(4-fluorophenyl)quinoline as an off-white solid (2.55 g, 58%). 1H NMR (500 MHz, CDCl3) δ 8.93 (1H, d, J 2.2 Hz), 8.33 (1H, d, J 2.1 Hz), 8.24 (1H, s), 7.82-7.78 (2H, m), 7.71-7.69 (2H, m), 7.20 (2H, t, J 8.6 Hz).

Workup

  1. temperatureto cool to ca. 80° C.
  2. temperaturecooled to room temperature
  3. customThe orange solid was collected under suction
  4. washwashed with toluene
  5. extractionextracted with dichloromethane (2×50 mL)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customevaporated
  8. customto give a yellow solid
  9. customThis was purified by flash chromatography
  10. washeluting with 2:1 dichloromethane/isohexane, dichloromethane

Sources & evidence

ORD record
ord-c6f7cc262374466d80a3b2a1297b30ac
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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