6-Bromo-2-naphthalenol → 6-Bromo-1-chloronaphthalen-2-ol

HRID 645314Notes

Reaction equation

HRID 645314 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13]2>[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-].ClCCl>[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([Cl:1])=[C:15]([OH:20])[CH:14]=[CH:13]2

Participants

5

Reactant 2

HCID 271446-Bromo-2-naphthalenolHCID 31398Chlorosuccinimide

Product 1

HCID 220481596-Bromo-1-chloronaphthalen-2-olYield 95.4%

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6344DichloromethaneSolvent

Procedure

The compound (S1-2) was synthesized according to the method disclosed in Synlett., No. 18, 2837 (2005). 29.9 g of N-chlorosuccinic acid imide and 600 mL of dichloromethane were added to a reactor under a nitrogen atmosphere and cooled to 0° C., to which 2.6 g of zirconium(IV) chloride was added, and then 50 g of 6-bromo-2-naphthol (S-1) was added gradually. After heating to room temperature and stirred for 10 hours, the reaction mixture was washed with a saturated sodium bicarbonate aqueous solution and water and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. 55 g of 6-bromo-1-chloro-2-naphthol (S1-2) was obtained by recrystallization from a mixed solvent of toluene and heptane (1/1 by volume).

Workup

  1. customThe compound (S1-2) was synthesized
  2. additionwas added
  3. washthe reaction mixture was washed with a saturated sodium bicarbonate aqueous solution and water
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-92cd7dcadddb40bd8a1b9ccd7a910d46
Source dataset
uspto-grants-2010_04
Patent number
US07704409B2

Reaction notes

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