Boron trifluoride → 1-(6-Bromonaphthalen-2-yl)ethanone

HRID 35188

Reaction equation

HRID 35188 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[C:12](Cl)(=[O:14])[CH3:13].[Sn](Cl)(Cl)(Cl)Cl.B(F)(F)F.[Cl-].[Cl-].[Cl-].[Al+3].[N+](C1C=CC=CC=1)([O-])=O>[Cl-].[Cl-].[Zn+2].C(Cl)Cl.C(#N)C.C(=S)=S.[N+](C)([O-])=O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=2)[CH:3]=1

Participants

12

Reactant 6

HCID 6356Boron trifluorideHCID 6367Acetyl chlorideHCID 7416NitrobenzeneHCID 113722-BromonaphthaleneHCID 24287Tin tetrachlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 124330821-(6-Bromonaphthalen-2-yl)ethanone

Reagents, catalysts & solvents 5

HCID 3007855ZincchlorideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 6348Carbon DisulfideSolventHCID 6375NitromethaneSolvent

Procedure

The compound of formula (II), 2-bromonaphthalene, is reacted with about 1 to 4 molar equivalents, preferably about 1.5 molar equivalents, of an acetyl halide, preferably acetyl chloride, in the presence of about 0.1 to 15 molar equivalents, preferably about 5 to 7 molar equivalents, of a Friedel-Crafts catalyst such as ferric chloride, zinc dichloride, tin tetrachloride, boron trifluoride or preferably aluminum trichloride, in a suitable solvent such as nitromethane, carbon disulphide, acetonitrile, methylene chloride or preferably nitrobenzene. The reaction is conducted at a temperature of about 25°-100° C., preferably about 50° C., for about 1-24 hours, preferably about 4 hours, giving the compound of formula (III), 2-bromo-6-acetylnaphthalene. When the reaction is substantially complete, the product of formula (III) is isolated by conventional means, for example crystallization.

Sources & evidence

ORD record
ord-be2ca39314434b6fa3c8999557133e1c
Source dataset
uspto-grants-1988_08
Patent number
US04766127

Linked notes

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