Water → 4-(4-(2-Bromoethoxy)phenyl)butanoic acid methyl ester

HRID 1881031Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[Br:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:17][CH2:16][Br:15])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-(4-hydroxyphenyl)butanoic acid methyl ester (2) (2.6 g) from the previous step was dissolved in N,N′-dimethylformamide (30 mL), 1,2-dibromoethane (12.6 g) and potassium carbonate (3.7 g) were added, and stirred at 80° C. for two days. The reaction solution was poured into water, and extracted with ethyl acetate (100 mL). The organic layer was washed with water (50 mL) and saturated sodium chloride solution (50 mL). After drying on anhydrous sodium sulfate, filtration and vacuum concentration, the residue was purified by silica gel flash column chromatography (developing solvent: n-hexane:ethyl acetate=8:1) to give the above-identified compound (676 mg, yield 17%).

Workup

extractionextracted with ethyl acetate (100 mL)
washThe organic layer was washed with water (50 mL) and saturated sodium chloride solution (50 mL)
dry with materialAfter drying on anhydrous sodium sulfate, filtration and vacuum concentration
customthe residue was purified by silica gel flash column chromatography (developing solvent: n-hexane:ethyl acetate=8:1)

Sources & evidence

ORD record: ord-433c86b8941f4392817fff1c676c568f
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318781B2

Reaction notes

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