Potassium Carbonate → HCID 18671666, compound

HRID 1057647Notes

Reaction equation

[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([Cl:21])=[C:16]([OH:22])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:24][C:25]#[N:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([Cl:21])=[C:16]([O:22][CH2:24][C:25]#[N:26])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 9-benzyl-3-chloro-9H-carbazol-4-ol (0.227 g, 0.739 mmol), bromoacetonitrile (0.177 g, 1.48 mmol), potassium carbonate (0.204 g, 1.48 mmol), and DMF (2 mL) is heated at 85° C. for 4 h, then allowed to cool and stir at room temperature for 12 h. Additional bromoacetonitrile (0.177 g) and potassium carbonate (0.204 g) are added and the mixture is heated again at 85° C. for 2 h. After cooling, the mixture is combined with that from another experiment run in the same manner (starting with 0.15 g of 9-benzyl-3-chloro-9H-carbazol-4-ol) and the combined mixtures are partitioned between ethyl acetate-aq. ammonium chloride/brine and brine. The organic layer is dried over magnesium sulfate and concentrated to dryness. Chromatography on silica gel (55 mL) using ethyl acetate-hexane (10/90) gave 0.292 g of [(9-benzyl-3-chloro-9H-carbazol-4-yl)oxy]acetonitrile as a clear liquid. 1H NMR (CDCl3) δ5.07, 5.50, 7.11, 7.15, 7.25-7.47, 7.50, 8.34.

Workup

temperatureto cool
temperaturethe mixture is heated again at 85° C. for 2 h
temperatureAfter cooling
customthe combined mixtures are partitioned between ethyl acetate-aq
dry with materialThe organic layer is dried over magnesium sulfate
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-c00082179b724079ac1d7b9d9eb67a87
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06514968B1

Reaction notes

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