1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 49842241, compound

HRID 409711Notes

Reaction equation

HRID 409711 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[NH2:15][C:16]1[CH:35]=[CH:34][C:19]([O:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:22]=2)=[CH:18][C:17]=1[F:36]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[NH:15][C:16]2[CH:35]=[CH:34][C:19]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])[CH:22]=3)=[CH:18][C:17]=2[F:36])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 67253219Tert-butyl 4-(4-amino-3-fluorophenoxy)picolinate

Product 1

HCID 49842241HCID 49842241, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At room temperature, 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene (1.06 g, 4.77 mmol, 1.05 eq) was dissolved in dichloromethane (10 mL). A solution of tert-butyl 4-(4-amino-3-fluorophenoxy)picolinate (1.38 g, 4.54 mmol, 1 eq) in dichloromethane (50 mL) was added dropwise slowly. The resulted mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure, and the resulted solid was purified by column chromatography (dichloromethane: methanol=30:1) to give the title compound (1.9 g, purity 94%, yield 80%) as a reddish-brown solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulted solid was purified by column chromatography (dichloromethane: methanol=30:1)

Sources & evidence

ORD record
ord-6db5edf54d9d418c949506ab423ad001
Source dataset
uspto-grants-2014_06
Patent number
US08759531B2

Reaction notes

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