Potassium Carbonate → [5-(4-Bromo-2-formyl-phenoxy)-2-chloro-phenyl]-acetic acid ethyl ester

HRID 885288Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:7]=1[Cl:13])[CH3:2].[Br:15][C:16]1[CH:17]=[CH:18][C:19](F)=[C:20]([CH:23]=1)[CH:21]=[O:22].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[C:10]([O:12][C:19]2[CH:18]=[CH:17][C:16]([Br:15])=[CH:23][C:20]=2[CH:21]=[O:22])[CH:9]=[CH:8][C:7]=1[Cl:13])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

(2-Chloro-5-hydroxy-phenyl)-acetic acid ethyl ester (0.5 g, 2.3 mmol), 5-bromo-2-fluorobenzaldehyde (0.33 mL, 2.8 mmol), and potassium carbonate (0.5 g, 3.5 mmol) were combined in 1,4-dioxane (30 mL) and heated to 110° C. for 3 days. After work-up, the crude material was purified by silica gel chromatography (0-20% EtOAc in hexanes) to give the desired product (0.3 g).

Workup

customAfter work-up, the crude material was purified by silica gel chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-90133ec8e7394010a3a1f1c7239e28db
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242145B2

Reaction notes

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