Dimethylformamide → Ethyl 4-bromo-3,5-diethoxybenzoate

HRID 401207Notes

Reaction equation

[Br:1][C:2]1[C:10](O)=[CH:9]C(C(O)=O)=[CH:4][C:3]=1[OH:12].[CH2:13](I)[CH3:14].[C:16]([O-:19])([O-])=O.[K+].[K+].[CH3:22][CH2:23][O:24][C:25]([CH3:27])=[O:26].[CH3:28]N(C=O)C>>[Br:1][C:2]1[C:3]([O:12][CH2:13][CH3:14])=[CH:4][C:27]([C:25]([O:24][CH2:23][CH3:22])=[O:26])=[CH:9][C:10]=1[O:19][CH2:16][CH3:28]

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 6340Iodoethane

HCID 8857Ethyl Acetate

HCID 11430Potassium Carbonate

HCID 860234-Bromo-3,5-dihydroxybenzoic acid

Product 1

HCID 10663268Ethyl 4-bromo-3,5-diethoxybenzoateYield 93%

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-bromo-3,5-dihydroxybenzoic acid (2.0 g, 8.6 mmol), EtI (6.7 g, 43.0 mmol) and K2CO3 (5.9 g, 43.0 mmol) in DMF (20 mL) was stirred at 50° C. overnight. Followed standard aqueous/EtOAc workup (2.5 g, yield 93%).

Sources & evidence

ORD record: ord-b3a4733070c34fdf8ab7ff74be89e611
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741915B2

Reaction notes

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