Methyl 3-(bromomethyl)benzoate → 3-(2-Bromo-6-ethoxy-4-formylphenoxymethyl)-benzoic acid methyl ester

HRID 910744Notes

Reaction equation

HRID 910744 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][CH3:13])[C:9]=1[OH:10])[CH:5]=[O:6].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23]Br)[CH:18]=1>>[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:10][C:9]2[C:8]([O:11][CH2:12][CH3:13])=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=2[Br:1])[CH:18]=1

Participants

3

Reactant 2

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehyde

Product 1

HCID 866244083-(2-Bromo-6-ethoxy-4-formylphenoxymethyl)-benzoic acid methyl ester

Procedure

Alkylation of 3-bromo-5-ethoxy-4-hydroxy benzaldehyde (2 g) with 3-bromomethyl-benzoic acid methyl ester (2.06 g) was performed according to the method described in example 1a. The residue was chromatographed on silica gel in heptane/ethyl acetate=7/3 (v/v) as eluent. Yield: 2.42 g. MS-ESI: [M+H]+=393/395

Workup

  1. customThe residue was chromatographed on silica gel in heptane/ethyl acetate=7/3 (v/v) as eluent

Sources & evidence

ORD record
ord-f4d371f3b8a146428db3ec7f787ef37f
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

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