Water → methyl 2-fluoro-4-{[(6-nitro-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate

HRID 1879401Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][CH2:10]2)=[CH:6][C:5]=1[OH:13])([O-:3])=[O:2].Br[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([F:26])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:26][C:18]1[CH:17]=[C:16]([CH2:15][O:13][C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:10][CH2:9][CH2:8]3)[CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

Conditions

Temperature: 50 °C

Procedure

7.17 g of 6-nitroindan-5-ol was dissolved in 80.0 mL of DMF, and 10.9 g of methyl 4-(bromomethyl)-2-fluorobenzoate and 6.63 g of potassium carbonate were added thereto, followed by stirring at 50° C. overnight. To the reaction liquid was added water, followed by extraction with ethyl acetate, and the organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1) to obtain 11.1 g of methyl 2-fluoro-4-{[(6-nitro-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate.

Workup

customTo the reaction liquid
extractionfollowed by extraction with ethyl acetate
washthe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record: ord-ff8ba60c1f1a4744b3f955cf9c19a179
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314240B2

Reaction notes

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