N-bromobutanimide → HCID 68621642, compound

HRID 2095217Notes

Reaction equation

[P:1]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[CH:11]([F:13])[F:12])=[O:2].[Br:20]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[P:1]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:20])=[CH:6][C:5]=1[CH:11]([F:13])[F:12])=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

200 mg of 2-(difluoromethyl)-4-methylphenyl diethyl phosphate (4C) was added to a solution of N-bromosuccinimide (254 mg) in benzene (10 mL), followed by the addition of benzoyl peroxide (3.2 mg). The reaction mixture was refluxed at 80° C. for about 48 hours and then cooled to room temperature and the succinimide residue removed by filtration. The filtrate was then washed successively with an aqueous solution of sodium bicarbonate, water, dried over anhydrous sodium sulfate, and concentrated by rotary evaporation. Subsequent flash column chromatography afforded a light yellow oily liquid (177 mg, 70%): 1H-NMR (CDCl3, 500 MHz) δ 7.7 (s, 1H), 7.6 (d, J=8.4 Hz, 1H), 7.3 (d, J=8.4 Hz, 1H), 6.8-6.9 (t, J=5.6 Hz, 1H), 4.5 (s, 2H), 4.2 (q, 4H), 1.3 (t, J=7.1 Hz, 6H) (FIG. 11). 13C-NMR (CDCl3, 50 MHz) δ 138.8, 130.4, 124.9, 120.4, 110.6, 65.1, 38.5, 15.9 (FIG. 12). 31P-NMR (CDCl3, 81 MHz) δ −6.57. 19F-NMR (CDCl3, 188.3 MHz) δ −116.3.

Workup

temperaturecooled to room temperature
customthe succinimide residue removed by filtration
washThe filtrate was then washed successively with an aqueous solution of sodium bicarbonate, water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record: ord-0ecb08bcb5c041549c323a54ff9a9aa4
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445706B2

Reaction notes

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