Sodium Iodide → Methyl 4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate

HRID 1520246Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:4]([CH3:16])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1.[I-].[Na+]>O.CC(N(C)C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:32][CH:33]=2)[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:4]([CH3:16])[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A reaction mixture of 4-bromo-1-(1-chloro-4,4,4-trifluorobutyl)-2-methylbenzene (369 g), sodium carbonate (245% g), methyl 4-aminobenzoate (194 g), sodium iodide (347 g) and DMA (1.2 L) was stirred at 50° C. for 3 hr. The reaction mixture was added to water. This reaction was performed for 3 batches, the obtained respective reaction mixtures were combined, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting solid was collected by filtration and washed with petroleum ether to give the title compound (1164 g).

Workup

customthe obtained respective reaction mixtures
extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
filtrationThe resulting solid was collected by filtration
washwashed with petroleum ether

Sources & evidence

ORD record: ord-d4e3c1bcb07e4e7abf3c98cd1d1a74d5
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073864B2

Reaction notes

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