3,4-Dichlorophenol → 3,4-Dichlorophenyl carbonochloridate

HRID 2371135Notes

Reaction equation

HRID 2371135 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].O=C(Cl)[O:12][C:13](Cl)(Cl)[Cl:14].C(N(CC)C(C)C)(C)C>ClCCl>[Cl:14][C:13]([O:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)=[O:12]

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 10426DiphosgeneHCID 81531Diisopropylethylamine

Product 1

HCID 130778903,4-Dichlorophenyl carbonochloridate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

3,4-Dichlorophenol (2.35 g) was dissolved in anhydrous dichloromethane (50 ml) at room temperature under an atmosphere of argon. The mixture was cooled to −30° C. and diphosgene (3.92 g) and N,N-Diisopropylethylamine (2.51 ml) were added slowly in the order specified. The resulting solution was then stirred at 0° C. for 3 hours, then at room temperature for 18 hours and finally at reflux for 2 hours. The solution volume was measured and used accordingly.

Workup

  1. waitat room temperature for 18 hours
  2. temperaturefinally at reflux for 2 hours

Sources & evidence

ORD record
ord-8c236df65e86444da2d0bc86560f7772
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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