Ethyl bromoacetate → HCID 86688755, compound

HRID 871047Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH2:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[C:6]([CH:14]=1)[CH2:7][N:8]1[CH:12]=[CH:11][C:10]([OH:13])=[N:9]1.[CH2:22]([O:24][C:25](=[O:28])[CH2:26]Br)[CH3:23].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:22]([O:24][C:25](=[O:28])[CH2:26][O:13][C:10]1[CH:11]=[CH:12][N:8]([CH2:7][C:6]2[CH:14]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[O:15][CH2:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[N:9]=1)[CH3:23]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 1-[5-bromo-2-(2-ethyl-butoxy)-benzyl]-1H-pyrazol-3-ol, 3, 0.06 g (0.15 mmol) in acetone (3 mL) was added ethylbromoacetate (24 μL 0.22 mmol), K2CO3 (0.03 g, 0.22 mmol) and tetrabutylammonium iodide (0.008 g, 0.022 mmol). The resulting mixture was heated at 120° C. in an Emrys microwave reactor for 20 min. The volatiles were removed in vacuo and the crude product was purified on silica to yield to {1-[5-Bromo-2-(2-ethyl-butoxy)-benzyl]-1H-pyrazol-3-yloxy}-acetic acid ethyl ester, 4.

Workup

customThe volatiles were removed in vacuo
customthe crude product was purified on silica

Sources & evidence

ORD record: ord-20c59bb02b674bdba1748b6686eb8cf8
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969589B2

Reaction notes

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