Sodium Carbonate → 2-Bromo-9H-carbazole

HRID 1022357Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)=[CH:4][CH:3]=1.C(OP(OCC)OCC)C.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:14][C:4]=2[CH:3]=1

Participants

Reactant 4

HCID 10340Sodium Carbonate

HCID 14798Sodium Hydroxide

HCID 31215Triethyl phosphite

HCID 218576474'-Bromo-2-nitrobiphenyl

Product 1

HCID 127170892-Bromo-9H-carbazoleYield 47.1%

Procedure

4′-bromo-2-nitrobiphenyl (9.8 g, 35.4 mmol) was refluxed with 30 mL triethylphosphite overnight. After cooling down the solution to room temperature, 40 mL 6(N)HCl was added to it slowly and heated to 80° C. for 3 h. Acidic solution was halfway neutralized with conc. NaOH, rest of the acidic solution was neutralized with solid Na2CO3. Cloudy solution was extracted three times with ethylacetate (500 mL). Combined organic layer was evaporated under vacuum and crude was flashed on silica gel (15% to 30% ethylacetate/hexane). 4.1 g final compound was isolated as off white solid.

Workup

temperatureheated to 80° C. for 3 h
extractionCloudy solution was extracted three times with ethylacetate (500 mL)
customCombined organic layer was evaporated under vacuum and crude

Sources & evidence

ORD record: ord-38e095ac6bfb47ff840b1666fc1e5c94
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722205B2

Reaction notes

Loading…