Sodium Thiosulfate → Methyl 5-bromo-4-cyclopropyl-2-ethoxybenzoate

HRID 531052Notes

Reaction equation

[Br:1]N1C(=O)NC(=O)N(Br)C1=O.[CH:12]1([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([O:25][CH2:26][CH3:27])[CH:16]=2)[CH2:14][CH2:13]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[Br:1][C:24]1[C:15]([CH:12]2[CH2:14][CH2:13]2)=[CH:16][C:17]([O:25][CH2:26][CH3:27])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

Conditions

Temperature: 90 °C

Procedure

Dibromoisocyanuric acid (2.54 g) was added at room temperature to a DMF (60 mL) solution of methyl 4-cyclopropyl-2-ethoxybenzoate (3.25 g), and the mixture was stirred at 90° C. for 1 hour in a nitrogen atmosphere. Dibromoisocyanuric acid (423 mg) was added to the reaction mixture, and the mixture was stirred at 90° C. for 30 minutes in a nitrogen atmosphere. An aqueous sodium thiosulfate solution was added to the reaction mixture at room temperature, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (4.08 g).

Workup

stirringthe mixture was stirred at 90° C. for 30 minutes in a nitrogen atmosphere
extractionfollowed by extraction with ethyl acetate
washThe obtained organic layer was washed with water and saturated saline in this order
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-9d56ae351139486d92a4cd80bc469fa5
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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