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

HRID 1521630Notes

Reaction equation

HRID 1521630 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

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 6-bromo-8-fluoro-3,4-dihydroquinolin-2(1H)-one (109-3; 8 g, 0.032 mol) in toluene (30 mL) was added Lawesson's reagent (13.26 g, 0.032 mol). Reaction mass was refluxed at 100° C. for 12 h. The reaction mixture was concentrated and directly purified by silica gel column chromatography to obtain title compound. MS (M+1): 262.0.

Workup

  1. customReaction mass
  2. concentrationThe reaction mixture was concentrated
  3. customdirectly purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e3c44ff3e03844d5bf330e1e3a6800c5
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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