Pyridine → (3-Bromo-5-iodo-phenyl)-carbamic acid methyl ester

HRID 1784885Notes

Reaction equation

HRID 1784885 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([I:9])[CH:8]=1)[NH2:5].N1C=CC=CC=1.Cl[C:17]([O:19][CH3:20])=[O:18]>C(Cl)Cl>[CH3:20][O:19][C:17](=[O:18])[NH:5][C:4]1[CH:6]=[C:7]([I:9])[CH:8]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 454803883-Bromo-5-iodoaniline

Product 1

HCID 68843615(3-Bromo-5-iodo-phenyl)-carbamic acid methyl esterYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-bromo-5-iodo-aniline (0.60 g, 2.01 mmol) and pyridine (0.65 mL, 8.06 mmol) in CH2Cl2 (15 mL) at 0° C. was added methyl chloroformate (0.17 mL, 2.22 mmol). The reaction mixture was allowed to warm to room temperature and was stirred for 12 hours. The reaction mixture was washed with twice with 5 mL 1 M HCl and 5 mL brine. The organic layer was dried over Na2SO4 and concentrated to give 0.71 g (99%) of (3-bromo-5-iodo-phenyl)-carbamic acid methyl ester.

Workup

  1. washThe reaction mixture was washed with twice with 5 mL 1 M HCl and 5 mL brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5d996fc57382415498ebbc3808665e3b
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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