Imidazole → HCID 137329871, compound

HRID 2223337Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[C:25]([C@H:29]1[CH2:38][CH2:37][C@H:36]2[C@@:39]3([CH:59]=[CH2:60])[C@H:48]([C@@H:49]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]O)[CH2:50][C@:30]12[CH2:31][O:32][SiH:33]([CH3:35])[CH3:34])[C:47]1[CH:46]=[CH:45][C:44]([O:57][CH3:58])=[CH:43][C:42]=1[CH2:41][CH2:40]3)([CH3:28])([CH3:27])[CH3:26].[Br:61]C(Br)(Br)Br>ClCCl>[Br:61][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][C@H:49]1[CH2:50][C@@:30]2([CH2:31][O:32][SiH:33]([CH3:35])[CH3:34])[C@@H:36]([CH2:37][CH2:38][C@@H:29]2[C:25]([CH3:26])([CH3:28])[CH3:27])[C@@:39]2([CH:59]=[CH2:60])[C@H:48]1[C:47]1[CH:46]=[CH:45][C:44]([O:57][CH3:58])=[CH:43][C:42]=1[CH2:41][CH2:40]2

Participants

Conditions

Temperature: 0 °C

Procedure

1.62 g of triphenylphosphine and 420 mg of imidazole are added in succession to a solution of 2.11 g of alcohol 8 in 41 ml of dichloromethane. The solution is cooled to 0° C., and 2.05 g of tetrabromomethane is added. The reaction mixture is heated to room temperature and stirred until the reaction is completed. For working-up, it is diluted with dichloromethane, the organic phase is washed with water and saturated sodium chloride solution, dried on magnesium sulfate and concentrated by evaporation. Column-chromatographic purification (cyclohexane/ethyl acetate) yields 2.3 g of bromide 10 as a colorless, viscous mass (GC-MS: m/z theor.: 574, pract.: 574).

Workup

temperatureThe reaction mixture is heated to room temperature
washthe organic phase is washed with water and saturated sodium chloride solution
customdried on magnesium sulfate
concentrationconcentrated by evaporation
customColumn-chromatographic purification (cyclohexane/ethyl acetate)

Sources & evidence

ORD record: ord-823907c90fc149d78a0d5d2ddf41daf0
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375098B2

Reaction notes

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