Bromine → 8-Bromo-7-hydroxyquinoline

HRID 2063553Notes

Reaction equation

HRID 2063553 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Br:12]Br>CC(O)=O.C(Cl)Cl.CCOC(C)=O>[Br:12][C:11]1[C:2]([OH:1])=[CH:3][CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

6

Reactant 2

HCID 24408BromineHCID 1354268667-Hydroxyquinoline

Product 1

HCID 1358901048-Bromo-7-hydroxyquinolineYield 76%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

To a stirred solution of 7-hydroxyquinoline (59.0 g, 0.406 mol) in AcOH (120 mL) and CH2Cl2 (240 mL) was slowly added bromine (22.9 ml, 0.444 mol) in AcOH (120 ml) while keeping the internal temperature at 0-5° C. The resulting suspension was stirred for 2 h at 0-5° C., and then diluted with EtOAc (100 mL) and filtered. The solid was washed with EtOAc (2×20 mL) and dried in vacuo to give 8-bromo-7-hydroxyquinoline (65 g, 76%).

Workup

  1. customat 0-5° C
  2. filtrationfiltered
  3. washThe solid was washed with EtOAc (2×20 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-840fc50e9dac485c815a3f44b46ba8e7
Source dataset
uspto-grants-2012_10
Patent number
US08288373B2

Reaction notes

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