Hydrogen Bromide → 6-Bromo-1-chloronaphthalen-2-ol

HRID 1400314Notes

Reaction equation

HRID 1400314 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12].[BrH:13]>CO.OO>[Br:13][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([Cl:1])=[C:3]([OH:12])[CH:4]=[CH:5]2

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 124591-Chloro-2-naphthol

Product 1

HCID 220481596-Bromo-1-chloronaphthalen-2-ol

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideSolventHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 400 mg (2.24 mmol) of 1-chloronaphthalen-2-ol in 3 mL of MeOH, HBr (purum p.a., ≧62%, 270 μL) and H2O2 (50 wt. % in water solution, 27 μL) were added. The resulting mixture was heated at 40° C. and stirred overnight. The mixture was quenched with water (10 mL) and extracted with ethyl acetate (10 mL×2). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 6-bromo-1-chloronaphthalen-2-ol as pale yellow solid which was used in the next step without further purification. HPLC-MS (ESI+): m/z 258.51 [M+H+].

Workup

  1. customThe mixture was quenched with water (10 mL)
  2. extractionextracted with ethyl acetate (10 mL×2)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9078dd4278fc4761b10edbc740a437f8
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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