N-bromobutanimide → N-[4-(Bromomethyl)-3-(trifluoromethyl)phenyl]-2,2,2-trifluoroacetamide

HRID 1993566Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[CH:4][C:3]=1[C:15]([F:16])([F:17])[F:18]

Participants

Conditions

Temperature: 85 °C

Procedure

Under N2-atmosphere, a suspension of N-(4-methyl-3-trifluoromethyl-phenyl)2,2,2-trifluoro-acetamide (Stage 128.4; 5.21 g, 19.2 mmol), N-bromosuccinimide (15 g, 84 mmol) and azo-iso-butyronitrile (740 mg, 4.5 mmol) in 430 ml of CCl4 is heated to 85° C. for 15 h. The hot mixture is filtered, the solid washed with CCl4 and discarded. The filtrate is concentrated, the residue re-dissolved in CH2Cl2 (0.7 L) and washed twice with 0.5 M solution of Na2S2O3 and brine. The inorganic phases are extracted with 2 portions of CH2Cl2, the organic phases dried (Na2SO4) and concentrated. Column chromatography (SiO2; hexane/CH2Cl2 1:1) yields the title compound: 1H-NMR (DMSO-d6): 11.59 (s, HN), 8.06 (d, 1H), 7.97 (dd, 1H), 7.76 (d, 1H), 4.77 (s, 2H).

Workup

filtrationThe hot mixture is filtered
washthe solid washed with CCl4
concentrationThe filtrate is concentrated
dissolutionthe residue re-dissolved in CH2Cl2 (0.7 L)
washwashed twice with 0.5 M solution of Na2S2O3 and brine
extractionThe inorganic phases are extracted with 2 portions of CH2Cl2
dry with materialthe organic phases dried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-4f9ec0b6ce5446aa99353a582261a626
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652022B2

Reaction notes

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