Pyridine → 1-Fluoro-2-isocyanato-4-methoxy-5-methyl-benzene

HRID 1691815Notes

Reaction equation

HRID 1691815 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH2:11].N1C=CC=CC=1.[C:18](Cl)(Cl)=[O:19]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[N:11]=[C:18]=[O:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 593777852-Fluoro-5-methoxy-4-methylaniline

Product 1

HCID 593778971-Fluoro-2-isocyanato-4-methoxy-5-methyl-benzene

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

2-Fluoro-5-methoxy-4-methyl-phenylamine (78 mg, 0.50 mmol) was dissolved in 10 ml of toluene at room temperature. DMAP (1 eq, 61 mg), pyridine (1.3 eq, 0.06 ml) were added followed by phosgene (1.33 eq, 0.34 ml, 20% solution in toluene). The mixture was allowed to stir at room temperature for 3 hours, forming a fine white precipitate. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was diluted with dichloromethane and concentrated in vacuo again to give 1-fluoro-2-isocyanato-4-methoxy-5-methyl-benzene (90 mg, quantitative) as a clear oil.

Workup

  1. customforming a fine white precipitate
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with dichloromethane
  5. concentrationconcentrated in vacuo again

Sources & evidence

ORD record
ord-342da76530f74e97a896651691cf49f5
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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