N-bromobutanimide → Ethyl 4-(bromomethyl)-3-(trifluoromethyl)benzoate

HRID 1946310Notes

Reaction equation

[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[C:13]([F:16])([F:15])[F:14].C1C(=O)N([Br:24])C(=O)C1.C(OOCC1C=CC=CC=1)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:24][CH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[C:13]([F:15])([F:14])[F:16]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of ethyl 4-methyl-3-(trifluoromethyl)benzoate (for a preparation see Intermediate 19)(2.25 g, 9.69 mmol) in carbon tetrachloride (25 ml) was added NBS (1.90 g, 10.7 mmol, Aldrich) and then benzyl peroxide (0.030 g, 0.124 mmol, Acros). The suspension was heated overnight at 90° C. under nitrogen. The suspension was filtered through a hydrophobic frit and the residue washed with carbon tetrachloride (10 ml). The filtrate was concentrated in vacuo to leave a mobile colourless oil (3.1 g). The residue was loaded in dichloromethane and purified on silica (100 g×2) using 0-100% dichloromethane-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white crystalline solid (1.6 g). LCMS: (System 4) MH+=312, tRET=3.32 min

Workup

filtrationThe suspension was filtered through a hydrophobic frit
washthe residue washed with carbon tetrachloride (10 ml)
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-7009483893894e39b9763f88d038136f
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399436B2

Reaction notes

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