Sulfuric Acid → 2-Bromo-1-(5-bromo-6-methoxynaphthalen-2-yl)propan-1-one

HRID 35033Notes

Reaction equation

[Br:1][CH:2]([C:4]1([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:26][CH3:27])[C:21]=3[Br:25])[CH:16]=2)O[C@@H](C(O)=O)[C@H](C(O)=O)[O:5]1)[CH3:3].S(=O)(=O)(O)O>>[Br:1][CH:2]([CH3:3])[C:4]([C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:26][CH3:27])[C:21]=2[Br:25])[CH:16]=1)=[O:5]

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 139009502-(1-bromoethyl)-2-(5-bromo-6-methoxy-2-naphthyl)-4(R),5(R)-dicarboxy-1,3-dioxolane

Product 1

HCID 136959262-Bromo-1-(5-bromo-6-methoxynaphthalen-2-yl)propan-1-oneYield 43%

Procedure

A mixture of diastereoisomers of 2-(1-bromoethyl)-2-(5-bromo-6-methoxy-2-naphthyl)-4(R),5(R)-dicarboxy-1,3-dioxolane (RRS:RRR=93:7; 2.52 g; 5 mmoles) and 96% sulphuric acid (15 ml) is kept at 20° C. for 20 minutes. The reaction mixture is processed as described in Example 1. In this manner, pure 2-bromo-1-(5-bromo-6-methoxy-2-naphthyl)-propan-1-one is obtained (0.8 g; 2.15 mmoles; yield 43%).

Sources & evidence

ORD record: ord-24a2112ae95d43b297ce6a9db1a811d1
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04764642

Reaction notes

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