Phosgene → HCID 23036561, compound

HRID 1709699Notes

Reaction equation

HRID 1709699 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Cl:11])[C:3]=1[OH:12].[H-].[Na+].[C:15](Cl)([Cl:17])=[O:16]>O1CCCC1.C(Cl)Cl>[Cl:17][C:15]([O:12][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][C:4]=1[Cl:11])=[O:16]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 120662,6-Dichloro-4-nitrophenolHCID 24758Sodium hydride

Product 1

HCID 23036561HCID 23036561, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,6-dichloro-4-nitrophenol (5.0 g, 24.0 mmol) in 10 ml of tetrahydrofuran is added dropwise to a suspension of sodium hydride (1.33 g, 50% NaH, 27.6 mmol) in 20 ml of THF. After the addition, stirring is continued for 1 hour at RT and is the mixture is then added dropwise to a solution of phosgene (14.0 g) in 50 ml of methylene chloride at -10°. The mixture is allowed to warm to RT and is purged with N2 to remove excess phosgene. The solvent is stripped and the residue is taken into methylene chloride. The precipitated sodium chloride is filtered and the filtrate is concentrated to give 2,6-dichloro-4-nitrophenyl chloroformate.

Workup

  1. additionAfter the addition
  2. customis purged with N2
  3. customto remove excess phosgene
  4. filtrationThe precipitated sodium chloride is filtered
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-a1b0b1119dff4655931fa9db56b3972c
Source dataset
uspto-grants-1990_08
Patent number
US04950678

Reaction notes

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