Boron tribromide → HCID 22918354, compound

HRID 1376775Notes

Reaction equation

[NH:1]([C:8]1[CH:9]=[C:10]2[C:15](=[O:16])[NH:14][C:12](=[O:13])[C:11]2=[CH:17][C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)(Cl)Cl>[NH:1]([C:8]1[CH:9]=[C:10]2[C:15](=[O:16])[NH:14][C:12](=[O:13])[C:11]2=[CH:17][C:18]=1[NH:19][C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -30 °C

Procedure

To a solution of 359.4 mg (1 mmol) of 4-anilino-5-(4-methoxy-anilino)-phthalimide in 5 ml of chloroform, a solution of 186 μl (2 mmol) boron tribromide is added dropwise at -40° C. to -30° C. The reaction mixture is stirred for 5 hours at -30° C., and is then quenched with 5 ml of water. The reaction mixture is warmed up to room temperature, and the phases are separated. The organic phase is washed twice with water, dried over magnesium sulfate and concentrated by evaporation. Excluding light, the evaporation residue is chromatographed with ethylacetate/hexane 1:1 on a silica gel column that is cooled with ice-water (double jacket), the product fractions are combined and concentrated by evaporation. The title compound is obtained in the form of yellow crystals, FAB-MS: 346 [M+ +H].

Workup

customis then quenched with 5 ml of water
temperatureThe reaction mixture is warmed up to room temperature
customthe phases are separated
washThe organic phase is washed twice with water
dry with materialdried over magnesium sulfate
concentrationconcentrated by evaporation
customthe evaporation residue is chromatographed with ethylacetate/hexane 1:1 on a silica gel column that
temperatureis cooled with ice-water (double jacket)
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-98d4a3dd3c04485d868940a09cb7234a
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05663336

Reaction notes

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