Potassium Carbonate → Ethyl 3-(2-hydroxy-2-methylpropoxy)-4-bromobenzoate

HRID 2102893Notes

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(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22]([CH3:25])([OH:24])[CH3:23]>CN(C=O)C>[OH:24][C:22]([CH3:25])([CH3:23])[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]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 4-bromo-3-hydroxybenzoate (1.5 g, 6.12 mmol), potassium carbonate (5.07 g, 36.72 mmol) and 1-chloro-2-methylpropan-2-ol (0.75 mL, 7.34 mmol) were placed in 50 mL DMF and the reaction was heated at 80° C. for 18 h. The mixture was cooled and partitioned between EtOAc and water. The organic layer was separated, washed with water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated under vacuum to an oil. Purification by column chromatography on silica gel using EtOAc/hexane (0-50%) gave the product (0.5 g, 26%) as a yellow oil.

Workup

temperatureThe mixture was cooled
custompartitioned between EtOAc and water
customThe organic layer was separated
washwashed with water, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationthe filtrate was concentrated under vacuum to an oil
customPurification by column chromatography on silica gel

Sources & evidence

ORD record: ord-5398f02845a54f9caff94ec8944468e3
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576099B2

Reaction notes

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