1,3-Dichloro-2-isocyanatobenzene → Methyl 3,5-dibromo-4-[({[(2,6-dichlorophenyl)amino]carbonyl}oxy)methyl]benzoate

HRID 394214Notes

Reaction equation

HRID 394214 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:14])[C:11]=1[CH2:12][OH:13])[C:5]([O:7][CH3:8])=[O:6].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[N:23]=[C:24]=[O:25]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:14])[C:11]=1[CH2:12][O:13][C:24]([NH:23][C:17]1[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=1[Cl:15])=[O:25])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 22648140Methyl 3,5-dibromo-4-(hydroxymethyl)benzoate

Product 1

HCID 22648016Methyl 3,5-dibromo-4-[({[(2,6-dichlorophenyl)amino]carbonyl}oxy)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 3,5-dibromo-4-(hydroxymethyl)benzoate (11 g, 34 mmol, 1 eq) in CH2Cl2 (50 mL) was added 2,6-dichlorophenylisocyanate (7 g, 37.2 mmol, 1.1 eq) and 4-N,N-dimethylaminopyridine (few crystals). Stirred at rt. After 15 min, the flask was thick with precipitate. Added 50 L CH2Cl2 to facilitate stirring and let stir overnight. Removed the CH2Cl2 under reduced pressure. Triturated the residue with Et2O and collected the solids giving methyl 3,5-dibromo-4-[({[(2,6-dichlorophenyl)amino]carbonyl}oxy)methyl]benzoate.

Workup

  1. stirringto facilitate stirring
  2. stirringlet stir overnight
  3. customRemoved the CH2Cl2 under reduced pressure
  4. customTriturated the residue with Et2O
  5. customcollected the solids

Sources & evidence

ORD record
ord-8e25599ebed14410ae8cbb79c21141e8
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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