Hydrogen Bromide → 2-Bromo-1-(6-(4-(2-bromoacetyl)phenyl)quinolin-2-yl)ethanone

HRID 1471191Notes

Reaction equation

HRID 1471191 reaction equation
[Br-:1].[Br-:2].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:22]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[N:37]=[C:36]([C:41](=[O:43])[CH3:42])[CH:35]=[CH:34]3)=[CH:27][CH:26]=1)(=[O:24])[CH3:23].Br>C(O)(=O)C>[Br:1][CH2:42][C:41]([C:36]1[CH:35]=[CH:34][C:33]2[C:38](=[CH:39][CH:40]=[C:31]([C:28]3[CH:27]=[CH:26][C:25]([C:22](=[O:24])[CH2:23][Br:2])=[CH:30][CH:29]=3)[CH:32]=2)[N:37]=1)=[O:43]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 21124087PyridiniumtribromideHCID 584988521-(6-(4-Acetylphenyl)quinolin-2-yl)ethanone

Product 1

HCID 584987592-Bromo-1-(6-(4-(2-bromoacetyl)phenyl)quinolin-2-yl)ethanoneYield 77.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Pyridinium tribromide (221 mg, 0.691 mmol) was added to a suspension of 1-(6-(4-acetylphenyl)quinolin-2-yl)ethanone (100 mg, 0.346 mmol) and HBr (0.061 mL, 0.35 mmol) in acetic acid (3 mL) the reaction mixture was stirred at 70° C.) for 6 h. The reaction was concentrated under vacuum and the residue was partitioned between aq NaHCO3 (15 mL) and EtOAc (30 mL+10 mL+10 mL). The organic layers were combined, washed with brine, dried, filtered and concentrated to yield crude 2-bromo-1-(6-(4-(2-bromoacetyl)phenyl)quinolin-2-yl)ethanone (120 mg) as white solid. LC-MS retention time 4.138 min; m/z 448.01 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 3u C18 2.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 0.8 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where Solvent A was 10% MeOH/90% H2O/0.1% trifluoroacetic acid and Solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a MICROMASS® Platform for LC in electrospray mode.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue was partitioned between aq NaHCO3 (15 mL) and EtOAc (30 mL+10 mL+10 mL)
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7bb62ae5b1c046aabd3b0cf8aced1143
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Reaction notes

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