Potassium Carbonate → [3-(4-Bromo-2-formyl-phenoxy)-4-methoxy-phenyl]acetic acid ethyl ester

HRID 656745Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([OH:14])[CH:7]=1)[CH3:2].[Br:16][C:17]1[CH:18]=[CH:19][C:20](F)=[C:21]([CH:24]=1)[CH:22]=[O:23].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:20]2[CH:19]=[CH:18][C:17]([Br:16])=[CH:24][C:21]=2[CH:22]=[O:23])[CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

(3-Hydroxy-4-methoxy-phenyl)-acetic acid ethyl ester (2.0 g, 9.5 mmol), 5-bromo-2-fluorobenzaldehyde (2.0 g, 9.5 mmol), and potassium carbonate (2.0 g, 14.3 mmol) were combined in 1,4-dioxane and heated to 90° C. overnight. After work-up, the crude material was purified by silica gel chromatography (0-25% EtOAc in hexanes) to give the desired product (1.8 g).

Workup

customAfter work-up, the crude material was purified by silica gel chromatography (0-25% EtOAc in hexanes)

Sources & evidence

ORD record: ord-c4d7e6b90e0a4705b1c643e762d88aff
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071807B2

Reaction notes

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