Water → 3-(6-Bromo-2-methoxy-quinolin-4-yl)-phenol

HRID 50172Notes

Reaction equation

HRID 50172 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:13])[CH:6]=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20]C)[CH:15]=1.B(Br)(Br)Br.O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:13])[CH:6]=[C:5]2[C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 224653996-Bromo-4-(3-methoxy-phenyl)2-methoxy-quinoline

Product 1

HCID 224654253-(6-Bromo-2-methoxy-quinolin-4-yl)-phenolYield 50.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-bromo-4-(3-methoxy-phenyl)2-methoxy-quinoline (1.31 g, 3.81 mmol) in dichloromethane (CH2Cl2. 30 ml) was added a solution of BBr3 in CH2Cl2 (1 M, 11.4 ml, 1 1.4 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 4 hours. It was poured into water. The organic layer was washed with brine, dried over MgSO4 and concentratred to give the tiltle compound of example 34A (640 mg, 41% yield).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-1f73bfff61394566acc19ac7f74e833a
Source dataset
uspto-grants-2004_03
Patent number
US06710209B2

Reaction notes

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