1-(Chloromethoxy)-2-methoxyethane → Methyl 3-bromo-5-formyl-4-(2-methoxyethoxymethoxy)-benzoate

HRID 1752877Notes

Reaction equation

HRID 1752877 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:13]=[O:14])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[CH3:15][O:16][CH2:17][CH2:18][O:19][CH2:20]Cl>>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:13]=[O:14])[C:11]=1[O:12][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[C:5]([O:7][CH3:8])=[O:6]

Participants

3

Reactant 2

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 71711084Methyl 3-bromo-5-formyl-4-hydroxybenzoate

Product 1

HCID 86607700Methyl 3-bromo-5-formyl-4-(2-methoxyethoxymethoxy)-benzoateYield 96%

Procedure

Proceeding as in Reference 12, but substituting methyl 3-bromo-5-formyl-4-hydroxybenzoate (12.6 g, 48.6 mmol, 1.0 eq.) and methoxyethoxymethyl chloride (6.8 mL, 7.26 g, 58.3 mmol, 1.2 eq.), gave methyl 3-bromo-5-formyl-4-(2-methoxyethoxymethoxy)-benzoate (16.2 g) as a colorless oil which solidified upon standing.

Sources & evidence

ORD record
ord-d809db375e2c43d28928f0fb88893fba
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

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