Bromine → 8-Bromo-7-hydroxyquinoline

HRID 532827Notes

Reaction equation

HRID 532827 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-345ecdd3f4324901a4b5494a24d3c373
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

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