Phosgene → HCID 28332426, compound

HRID 1470773Notes

Reaction equation

HRID 1470773 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](Cl)(Cl)=[O:14]>O1CCOCC1>[Br:11][C:10]1[C:2]2[NH:1][C:13](=[O:14])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=[C:8]([Cl:12])[CH:9]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 117799312-Amino-3-bromo-5-chlorobenzoic acid

Product 1

HCID 28332426HCID 28332426, compoundYield 114.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-3-bromo-5-chlorobenzoic acid (10.0 g, 39.9 mmol) in dioxane (170 mL) was added phosgene (20% in toluene, 42.0 mL, 79.9 mmol) over a period of 15 mins. The reaction was stirred at ambient temperature for 48 h and then concentrated in vacuo. The resulting solid was crushed and further dried in vacuo to yield the desired product (12.6 g, 114%) which was used in the subsequent step without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting solid was crushed
  3. customfurther dried in vacuo

Sources & evidence

ORD record
ord-5274d672fad64d94864db6103f7386d2
Source dataset
uspto-grants-2015_04
Patent number
US09006485B2

Reaction notes

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