Methanol → (E)-Methyl 2-(methoxyimino)-2-[2-(bromomethyl)phenyl]acetate

HRID 2038444Notes

Reaction equation

HRID 2038444 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][O:6][C:5]1=O.S(Br)([Br:17])=O.[CH3:19][OH:20]>>[CH3:19][O:20][C:5](=[O:6])/[C:4](/[C:13]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:7][Br:17])=[N:3]/[O:2][CH3:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 68176Thionyl bromideHCID 53927100HCID 53927100, compound

Product 1

HCID 10989774(E)-Methyl 2-(methoxyimino)-2-[2-(bromomethyl)phenyl]acetateYield 10%

Procedure

To a solution of isochroman-3,4-dione 4-(O-methyl-oxime) (5.6 g, 0.028 mol) in methanol (27 g) was added dropwise at 10-20° C. thionyl bromide (45.4 g, 0.22 mol) over a period of 1 h and the resulting mixture was stirred at ambient temperature overnight. The reaction was monitored by HPLC. Concentration of the mixture in vacuo led to a crude residue (14.2 g). A small amount of the residue (3.2 g) was purified by silica column chromatography to yield (2-bromomethyl-phenyl)-[(E)-methoxyimino]-acetic acid methyl ester as a colorless solid (0.8 g).

Workup

  1. customA small amount of the residue (3.2 g) was purified by silica column chromatography

Sources & evidence

ORD record
ord-c9cdb612d8be4159a844f1e9ee713a4c
Source dataset
uspto-grants-2013_11
Patent number
US08575366B2

Reaction notes

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