1-Bromo-3,5-bis(trifluoromethyl)benzene → 3',5'-Bis(trifluoromethyl)-2-aminobenzophenone

HRID 2090540Notes

Reaction equation

CON(C)[C:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7].[F:14][C:15]([F:28])([F:27])[C:16]1[CH:17]=[C:18](Br)[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.C([Li])CCC>O1CCCC1>[F:14][C:15]([F:27])([F:28])[C:16]1[CH:17]=[C:18]([C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[NH2:7])[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Then, in a nitrogen atmosphere, N-methoxy-N-methyl-anthranilamide (0.62 g, 3.4 mmol), and 3,5-bis(trifluoromethyl)-1-bromobenzene (1.00 g, 3.4 mmol) were dissolved in tetrahydrofuran (20 mL), followed by stirring at −78° C. To the solution, 1.66 mol/L n-butyl lithium (4.11 mL, 6.8 mmol) was gradually added dropwise, followed by stirring for 30 minutes. The reaction was terminated by adding 1 mol/L hydrochloric acid. The reaction solution was extracted with ethyl acetate. The organic layer was washed with a sodium chloride solution and then dried with magnesium sulfate, followed by filtration. The filtrate was concentrated using a rotary evaporator. The residue was purified by recrystallization (hexane). Thus, 3′,5′-bis(trifluoromethyl)-2-aminobenzophenone (1.1 g, 3.3 mmol) was obtained in a yield of 96%.

Workup

stirringby stirring for 30 minutes
customThe reaction was terminated
additionby adding 1 mol/L hydrochloric acid
extractionThe reaction solution was extracted with ethyl acetate
washThe organic layer was washed with a sodium chloride solution
dry with materialdried with magnesium sulfate
filtrationfollowed by filtration
concentrationThe filtrate was concentrated
customa rotary evaporator
customThe residue was purified by recrystallization (hexane)

Sources & evidence

ORD record: ord-50704c5c022843f89b42e68fd22c924e
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436173B2

Reaction notes

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