Methanol → 2-Bromo-1-(6,7-dimethoxynaphthalen-2-yl)ethan-1-one

HRID 53225Notes

Reaction equation

HRID 53225 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[CH:11]=[C:10]([C:17](=[O:19])[CH3:18])[CH:9]=[CH:8]2.CO>C(Cl)(Cl)Cl>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[CH:11]=[C:10]([C:17](=[O:19])[CH2:18][Br:1])[CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 887MethanolHCID 24408BromineHCID 2811011-(6,7-dimethoxynaphthalen-2-yl)ethanone

Product 1

HCID 128492632-Bromo-1-(6,7-dimethoxynaphthalen-2-yl)ethan-1-oneYield 66.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of bromine (4.5 g, 0.029 mol) in chloroform (30 ml) is added dropwise to a solution of 6,7-dimethoxy-2-acetylnaphthalene (6.7 g, 0.029 mol) in a mixture chloroform (70 ml)/methanol (15 ml). Once the reaction mixture discoloures, it is concentrated to dryness and the residue is treated with a mixture ethyl ether/isopropyl ether. The thus obtained solid is triturated with methanol yielding 6,7-dimethoxy-2-(2-bromoacetyl)naphthalene (6 g). M.p. 120°-122° C.

Workup

  1. concentrationOnce the reaction mixture discoloures, it is concentrated to dryness
  2. additionthe residue is treated with a mixture ethyl ether/isopropyl ether
  3. customThe thus obtained solid is triturated with methanol

Sources & evidence

ORD record
ord-2782b5b8823b454584b2949b3a06c5ec
Source dataset
uspto-grants-1997_04
Patent number
US05618822

Reaction notes

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