1-Bromo-2-methoxynaphthalene → 2-Acetyl-6-methoxynaphthalene

HRID 1030842Notes

Reaction equation

HRID 1030842 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH3:20])[C:14]=2Br)[CH:9]=1)(=[O:7])[CH3:6].BrC1C2C(=CC=CC=2)C=CC=1OC>CC1C=CC(C)=CC=1>[C:5]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH3:20])[CH:14]=2)[CH:9]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 728601-Bromo-2-methoxynaphthaleneHCID 6221781-(5-Bromo-6-methoxynaphthalen-2-yl)ethan-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 775062-Acetyl-6-methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

45.3 Ml of p-xylene and 8.2 g of anhydrous aluminum chloride are added to the solution of 2-acetyl-5-bromo-6-methoxynaphthalene obtained as in example 1a), while keeping the temperature at -10° C. The reaction mixture is kept for 16 hours under stirring at room temperature and then it is worked as in example 1 obtaining 42.8 g of product with a yield equal to 87.3% calculated on the basis of the starting material 1-bromo-2-methoxynaphthalene.

Workup

  1. customobtained as in example 1a),
  2. customat -10° C

Sources & evidence

ORD record
ord-2f93aea472d243479a535e24734e7c06
Source dataset
uspto-grants-1992_04
Patent number
US05107013

Reaction notes

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