Acetyl chloride → 1-(4-Bromonaphthalen-1-yl)ethanone

HRID 354645Notes

Reaction equation

HRID 354645 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=O)=[CH:4][CH:3]=1.Br[C:16]1C2C(=CC=CC=2)C=CC=1.C(Cl)(=O)C>>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](=[O:14])[CH3:16])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 70011-BromonaphthaleneHCID 2825914-Bromo-1-naphthoic acid

Product 1

HCID 2305841-(4-Bromonaphthalen-1-yl)ethanone

Procedure

The 4-bromo-1-naphthoic acid required as starting material according to the process according to the invention has already been described in the literature. It can, for example, be prepared in a simple manner by reacting 1-bromonaphthalene with acetyl chloride in a Friedel-Crafts reaction to give 4-bromo-1-acetylnaphthalene (see K. Dziewouski and L. Sternback, Bull. acad. polonaise A, 1931, 59 to 68, or T. L. Jacobs, S. Winstein, J. W. Ralls and J. H. Robson Journ. org. chem. 11 (1946), 27-33) and by oxidation of the latter compound with hypochlorite [see T. L. Jacobs et. al, see above, or N. J. Leonard and A. M. Hyson, J. Am. chem. soc. 71 (1949), 1963].

Workup

  1. customin a Friedel-Crafts reaction

Sources & evidence

ORD record
ord-4d1a97d3d84144b9ae7def1c9139d946
Source dataset
uspto-grants-1983_03
Patent number
US04376214

Reaction notes

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