Triethyl phosphite → HCID 12532386, compound

HRID 1755510Notes

Reaction equation

HRID 1755510 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O.P(OCC)(OCC)OCC>>[Cl:10][C:6]1[C:5]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:1][C:4]=2[CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 15175504HCID 15175504, compound

Product 1

HCID 12532386HCID 12532386, compoundYield 36.4%

Conditions

Temperature
140 °C

Procedure

In a stream of nitrogen, a 500 mL egg-plant flask was charged with 60.0 g (257.4 mmol) of 2-nitro-6-chlorobiphenyl, obtained in Synthesis Example 1. The content was heated to 140° C., and 106 g of triethyl phosphite was dropwise added over 2 hours. After the dropwise addition, the content was further heated at 140° C. for 2 hours. Then triethyl phosphite was distilled off under reduced pressure. Toluene was added to the residue, and the thus-deposited solid was filtered. The thus-obtained crude product was purified by silica gel column chromatography using toluene as a developing solvent to give 18.9 g (93.72 mmol) of 4-chlorocarbazole as a white powder (yield: 36%).

Workup

  1. customobtained in Synthesis Example 1
  2. additionAfter the dropwise addition
  3. temperaturethe content was further heated at 140° C. for 2 hours
  4. distillationThen triethyl phosphite was distilled off under reduced pressure
  5. additionToluene was added to the residue
  6. filtrationthe thus-deposited solid was filtered
  7. customThe thus-obtained crude product
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e3dc9112abe04c9cb5d4889ea95b6334
Source dataset
uspto-grants-2015_10
Patent number
US09172045B2

Reaction notes

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