Methyl chloroformate → Methyl 4-bromo-2-iodophenylcarbamate

HRID 1481735Notes

Reaction equation

HRID 1481735 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([I:9])[CH:3]=1.Cl[C:11]([O:13][CH3:14])=[O:12]>N1C=CC=CC=1.O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11](=[O:12])[O:13][CH3:14])=[C:4]([I:9])[CH:3]=1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 8239344-Bromo-2-iodoaniline

Product 1

HCID 23643163Methyl 4-bromo-2-iodophenylcarbamateYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To solution of 4-bromo-2-iodoaniline (18.50 g, 62.08 mmol) in pyridine (120 mL) at −10° C. was added methyl chloroformate (7.50 mL, 97.46 mmol) over 30 min via syringe pump. Reaction was allowed to warm to room temperature and was diluted with H2O (450 mL). Solid which was formed was collected by filtration, washed with H2O and dried in dessicator. Methyl 4-bromo-2-iodophenylcarbamate (21.59 g, 98%) was obtained as colorless solid.

Workup

  1. customReaction
  2. customSolid which was formed
  3. filtrationwas collected by filtration
  4. washwashed with H2O
  5. customdried in dessicator

Sources & evidence

ORD record
ord-909e1832e88c46c0a182d3d103bbe4c3
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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