Phosphorus tribromide → 4-(1-Bromopropan-2-yloxy)-7-methoxyquinoline

HRID 1878698Notes

Reaction equation

HRID 1878698 reaction equation
COC1C=C2C(C(OCC(O)C)=CC=N2)=CC=1.[CH3:18][O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]([O:30][CH:31]([CH3:34])[CH2:32]O)=[CH:25][CH:26]=[N:27]2)=[CH:22][CH:21]=1.P(Br)(Br)[Br:36]>C(Cl)Cl>[Br:36][CH2:32][CH:31]([O:30][C:24]1[C:23]2[C:28](=[CH:29][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[N:27]=[CH:26][CH:25]=1)[CH3:34]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 688094362-(7-Methoxyquinolin-4-yloxy)propan-1-olHCID 688118821-(7-Methoxyquinolin-4-yloxy)propan-2-ol

Product 1

HCID 598430804-(1-Bromopropan-2-yloxy)-7-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(7-methoxyquinolin-4-yloxy)propan-2-ol (235 mg, 1007 μmol) and 2-(7-methoxyquinolin-4-yloxy)propan-1-ol (235 mg, 1007 μmol) (mixture of isomers) in CH2Cl2 (3 mL) was added phosphorus tribromide (94.7 μl, 1007 μmol). The mixture was heated to reflux for 18 h. The mixture was quenched with 5% NaHCO3, and was extracted with CH2Cl2 (3×5 mL). The combined organics were dried over MgSO4 and concentrated to a white solid (150 mg) under reduced pressure. MS (ESI pos. ion) m/z (MH+): 296/298. Calc'd exact mass for C13H14BrNO2: 295.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe mixture was quenched with 5% NaHCO3
  4. extractionwas extracted with CH2Cl2 (3×5 mL)
  5. dry with materialThe combined organics were dried over MgSO4
  6. concentrationconcentrated to a white solid (150 mg) under reduced pressure

Sources & evidence

ORD record
ord-7600bbd846b942b7be1d7395ff57d139
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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