Potassium Carbonate → HCID 68694827, compound

HRID 1169940Notes

Reaction equation

HRID 1169940 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([OH:12])[CH:6]=1.C([O-])([O-])=O.[K+].[K+].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1>CC#N>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([O:12][CH2:25][C:24]2[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 579787Methyl 3,5-dihydroxyphenylacetate

Product 1

HCID 68694827HCID 68694827, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3,5-Dihydroxy-phenyl)-acetic acid methyl ester (0.500 g, 2.75 mmol) in MeCN (5 ml) was treated with K2CO3 (0.095 g, 6.88 mmol) and 4-fluorobenzyl bromide (0.520 g, 2.75 mmol). The resultant mixture was stirred overnight at room temperature. The reaction mixture was directly purified by flash column chromatography (EtOAc:iso-hexane) to give [3-(4-fluoro-benzyloxy)-5-hydroxy-phenyl]-acetic acid methyl ester (0.15 g).

Workup

  1. customThe reaction mixture was directly purified by flash column chromatography (EtOAc:iso-hexane)

Sources & evidence

ORD record
ord-0db288a177d045ffb6f05e3f608a39ab
Source dataset
uspto-grants-2010_11
Patent number
US07825160B2

Reaction notes

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