Water → 2-(2,6-Dichlorophenyl)-6-quinolinol

HRID 1869798Notes

Reaction equation

HRID 1869798 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26])[CH:13]=[CH:12]2)C1C=CC=CC=1.B(Br)(Br)Br.O.[OH-].[Na+]>C(Cl)Cl>[Cl:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[C:19]=1[C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=2)[N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 579876386-(Benzyloxy)-2-(2,6-dichlorophenyl)quinoline

Product 1

HCID 579876402-(2,6-Dichlorophenyl)-6-quinolinolYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(benzyloxy)-2-(2,6-dichlorophenyl)quinoline 19 (2.5 g) in CH2Cl2 (20 ml) are added, at 0° C., 20 ml of BBr3 (1 M in CH2Cl2). The solution is stirred for 1 h at room temperature. Water (20 ml) is added and the resulting solution is alkalinized with 1 N NaOH. The aqueous phase is extracted with AcOEt (3×20 ml). The organic phases are washed with brine, dried over MgSO4 and evaporated. 2-(2,6-dichlorophenyl)-6-quinolinol 20 is obtained as a yellow solid and is used without further purification in the next step.

Workup

  1. extractionThe aqueous phase is extracted with AcOEt (3×20 ml)
  2. washThe organic phases are washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-48913fb574b844b2807a2fb18ee8ca45
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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