N-bromobutanimide → Methyl 3-bromo-5-formyl-4-hydroxybenzoate

HRID 1752871Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])=[O:2].[Br:14]N1C(=O)CCC1=O>>[Br:14][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([CH:1]=[O:2])[C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7]

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 212595Benzoic acid, 3-formyl-4-hydroxy-, methyl ester

Product 1

HCID 71711084Methyl 3-bromo-5-formyl-4-hydroxybenzoateYield 73%

Procedure

Proceeding as in Reference 9, but substituting methyl 3-formyl-4-hydroxybenzoate (12.0 g, 66.6 mmol, 1 eq.) and N-bromosuccinimide (12.45 g, 69.9 mmol, 1.05 eq.) gave methyl 3-bromo-5-formyl-4-hydroxybenzoate (12.6 g) as a white solid.

Sources & evidence

ORD record: ord-0ca128939f5f4bfeba422e0170f51a61
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162986B2

Reaction notes

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