N-bromobutanimide → Methyl 1-(4-(bromomethyl)phenyl)cyclopropanecarboxylate

HRID 332680Notes

Reaction equation

[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[Br:15]N1C(=O)CCC1=O>C(#N)C.O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:14][C:1]1[CH:2]=[CH:3][C:4]([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of methyl 1-(p-tolyl)cyclopropanecarboxylate (3 g, 15.77 mmol) in acetonitrile (42 mL), was added N-bromosuccinimide (2.807 g, 15.77 mmol) followed by benzoyl peroxide (0.164 g, 0.473 mmol). The reaction was stirred at 80° C. for 2 hours 40 minutes and then allowed to cool to room temperature. The reaction mixture was diluted with water and extracted with dichloromethane (×3). The combined organic extracts were washed with brine and dried (magnesium sulfate), filtered and concentrated under reduced pressure to afford a red oil. The crude material was purified by silica gel column chromatography eluting with 0-9% ethyl acetate in iso-hexane to afford the title compound (2.478 g, 58%).

Workup

temperatureto cool to room temperature
extractionextracted with dichloromethane (×3)
washThe combined organic extracts were washed with brine
dry with materialdried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated under reduced pressure
customto afford a red oil
customThe crude material was purified by silica gel column chromatography
washeluting with 0-9% ethyl acetate in iso-hexane

Sources & evidence

ORD record: ord-4487fec950234bb6af5842eb0385a672
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877774B2

Reaction notes

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