Lawesson's reagent → 6-bromo-8-fluoro-3,4-dihydroquinoline-2(1H)-thione

HRID 921969Notes

Reaction equation

HRID 921969 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[NH:8][C:7](=O)[CH2:6][CH2:5]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[NH:8][C:7](=[S:23])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 709774606-BROMO-8-FLUORO-3,4-DIHYDROQUINOLIN-2(1H)-ONE

Product 1

HCID 891560716-bromo-8-fluoro-3,4-dihydroquinoline-2(1H)-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 6-bromo-8-fluoro-3,4-dihydroquinolin-2(1H)-one (1-3, 2.00 g, 8.19 mmol) in toluene (50 mL) was added Lawesson's reagent (1.66 g, 4.10 mmol). After refluxing the reaction mixture for 2 h, the toluene was distilled off to yield the crude product, which was then purified by flash chromatography on silica gel to obtain the title compound as a yellow solid; 1H NMR (DMSO-D6, 500 MHz) δ=12.14 (s, 1H), 7.46 (dd, J=2.0 Hz, JHF=10.0 Hz, 1H), 7.34 (s, 1H), 2.94 (d, J=8.0 Hz, 2H), 2.84 (d, J=8.0 Hz, 2H).

Workup

  1. temperatureAfter refluxing the reaction mixture for 2 h
  2. distillationthe toluene was distilled off
  3. customto yield the crude product, which
  4. customwas then purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-14c2ac738c4a415183c33df998014ef7
Source dataset
uspto-grants-2016_03
Patent number
US09278093B2

Reaction notes

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