Benzyl Bromide → [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetic acid benzyl ester

HRID 1528825Notes

Reaction equation

HRID 1528825 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:26][N:25]=[C:24]([CH3:27])[C:23]=2[CH2:28][C:29]([OH:31])=[O:30])=[CH:18][CH:17]=1>>[CH2:1]([O:31][C:29](=[O:30])[CH2:28][C:23]1[C:24]([CH3:27])=[N:25][O:26][C:22]=1[C:19]1[CH:20]=[CH:21][C:16]([Br:15])=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7498Benzyl Bromide2×HCID 10796Cesium carbonateHCID 66577233[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetic acid

Product 1

HCID 66577402[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetic acid benzyl ester

Procedure

Benzyl bromide (0.491 mL, 4.13 mmol) and cesium carbonate (1.68 g, 5.16 mmol) were added to [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-acetic acid (1.02 g, 3.44 mmol) and the reaction stirred at room temperature. After two hours, a second aliquot of benzyl bromide (0.100 mL) was added. When the reaction was complete by analytical LCMS it was submitted to standard aqueous workup to obtain the title compound.

Sources & evidence

ORD record
ord-4664d99d8a184d20a478c63f766783f9
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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