Bromine → [3-Bromo-1-(4-chloro-phenyl)-2-oxo-cyclohexyl]-acetonitrile

HRID 2076008Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

1-(4-Chloro-phenyl)-2-oxo-cyclohexyl-acetonitrile (100 mg, 0.40 mmol) was dissolved in chloroform (1 mL). To this solution bromine (67.7 mg, 0.42 mmol) in chloroform (0.5 mL) was added drop wise at −11° C. The reaction was stirred for 1½ hours at 5° C., then for 1 hours t room temperature and finally for 1 hour at 50° C. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel using dichloromethane as eluent to yield the title compound (104 mg, 79%) as colourless oil. NMR (CDCl3, 300 MHz): δ (ppm)=7.44 (d, 2H), 7.13 (d, 2H), 4.62 (dd, 1H), 2.99 (m, 2.80 (s, 2H), 2.58 (m, 1H), 2.14 (m, 1H), 1.92 (m, 3H).

Workup

waitfinally for 1 hour at 50° C
customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-5a19e041e9f2485f8dd1062e8d0c5cc3
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923450B2

Reaction notes

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