Triethyl phosphite → 2-chloro-9H-carbazole

HRID 2120117Notes

Reaction equation

HRID 2120117 reaction equation
[Cl: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.P(OCC)(OCC)OCC>>[Cl: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

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 2355494'-Chloro-2-nitro-1,1'-biphenyl

Product 1

HCID 27523882-chloro-9H-carbazoleYield 69.2%

Conditions

Temperature
150 °C

Procedure

A mixture of 4′-Chloro-2-nitrobiphenyl (640 mg) and triethyl phosphite (1.9 ml) was heated at 150° C. for 3 hrs. The mixture was then allowed to cool and purified by flash chromatography (5-10% ethyl acetate/hexane) to afford the sub-title compound as a white solid (382 mg): 1H NMR (400 MHz, d6-DMSO) δ 7.12-7.23 (2H, m), 2.40 (1H, m), 7.46-7.54 (2H, m), 8.12 (2H, d).

Workup

  1. temperatureto cool
  2. custompurified by flash chromatography (5-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e335c4570e614e218465562edf5b0502
Source dataset
uspto-grants-2004_02
Patent number
US06689784B2

Reaction notes

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