Bromine → 5-Bromo-7-chloro-2-methylquinolin-6-ol

HRID 931699Notes

Reaction equation

HRID 931699 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][C:3]=1[OH:13].[Br:14]Br>C(O)(=O)C>[Br:14][C:4]1[C:3]([OH:13])=[C:2]([Cl:1])[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2

Participants

4

Reactant 2

HCID 24408BromineHCID 666314067-Chloro-2-methylquinolin-6-ol

Product 1

HCID 666313995-Bromo-7-chloro-2-methylquinolin-6-olYield 135.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 7-chloro-2-methylquinolin-6-ol (1C) (450 mg, 2.3 mmol) in acetic acid (15 mL) was added Br2 (0.13 mL, 2.4 mmol) at ambient temperature. The mixture was stirred at ambient temperature for 2 hours. The solid that formed was filtered and collected to give 1D as an off-white solid as the HBr salt (847 mg, 100%). LCMS-ESI+ (m/z): 281.1, 283.1 (M+H)+.

Workup

  1. customThe solid that formed
  2. filtrationwas filtered
  3. customcollected

Sources & evidence

ORD record
ord-004a15b9a8ca4b57a25185195e3b21ed
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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