Sodium hydride → Ethyl 3-{[4-(acetyloxy)butyl]oxy}-4-bromobenzoate

HRID 2100380Notes

Reaction equation

[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[OH:13].[C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21]I)(=[O:16])[CH3:15].[H-].[Na+]>CN(C=O)C>[C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[Br:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:16])[CH3:15]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 4-bromo-3-hydroxybenzoate (200 mg) was dissolved in DMF (10 ml) and 4-iodo-butyl acetate (195 μl) and sodium hydride (56 mg, 60% dispersion in mineral oil) were added and the reaction stirred at 80° C. under nitrogen for 3 hours. The reaction was quenched with water (5 ml) and the solvents evaporated under vacuum. The residue was partitioned between ethyl acetate/chloroform (1:1) and water. The organic phase was dried using a hydrophobic filter and the solvent evaporated in vacuo to give ethyl 3-{[4-(acetyloxy)butyl]oxy}-4-bromobenzoate as a yellow gel (318 mg).

Workup

customThe reaction was quenched with water (5 ml)
customthe solvents evaporated under vacuum
customThe residue was partitioned between ethyl acetate/chloroform (1:1) and water
customThe organic phase was dried
filtrationa hydrophobic filter
customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-b2c0cdb23dc54c23bd09b8b75e19bf34
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572790B2

Reaction notes

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