Potassium Hydroxide → [3-Bromo-4-(cyclopropylsulfanyl)phenyl]acetic acid

HRID 2192903Notes

Reaction equation

O.NN.[Br:4][C:5]1[CH:6]=[C:7]([C:15](=O)[C:16]([OH:18])=[O:17])[CH:8]=[CH:9][C:10]=1[S:11][CH:12]1[CH2:14][CH2:13]1.[OH-].[K+]>Cl>[Br:4][C:5]1[CH:6]=[C:7]([CH2:15][C:16]([OH:18])=[O:17])[CH:8]=[CH:9][C:10]=1[S:11][CH:12]1[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 80 °C

Procedure

To hydrazine monohydrate (16.9 mL) was added [3-bromo-4-(cyclopropylsulfanyl)phenyl](oxo)acetic acid (15 g) under ice-cooling, followed by stirring at 80° C. for 10 minutes. To the reaction mixture was added potassium hydroxide (8.22 g), followed by stirring at 80° C. for 20 minutes and then stirring at 100° C. overnight. After leaving it to be cooled at room temperature, concentrated hydrochloric acid (50 mL) was added thereto under ice-cooling, followed by extraction with chloroform (50 mL×3). The organic layer was sequentially washed with 1 M hydrochloric acid (50 mL×2) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure to obtain [3-bromo-4-(cyclopropylsulfanyl)phenyl]acetic acid (13.5 g) as a pale yellow solid.

Workup

temperaturecooling
stirringby stirring at 80° C. for 20 minutes
stirringstirring at 100° C. overnight
customAfter leaving it
temperatureto be cooled at room temperature
temperatureunder ice-cooling
extractionfollowed by extraction with chloroform (50 mL×3)
washThe organic layer was sequentially washed with 1 M hydrochloric acid (50 mL×2) and saturated brine (50 mL)
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record: ord-72975d8db82f45dab6909ee6b92eb0e1
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329707B2

Reaction notes

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