Benzene → HCID 14855598, compound

HRID 477415Notes

Reaction equation

HRID 477415 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:7]([O:16][C:17]2[CH:28]=[CH:27][C:20]([O:21][CH:22]([CH3:26])[C:23](O)=[O:24])=[C:19]([F:29])[CH:18]=2)=[N:8][CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1.C1C=CC=CC=1>CN(C)C=O>[Cl:5][C:6]1[C:7]([O:16][C:17]2[CH:28]=[CH:27][C:20]([O:21][CH:22]([CH3:26])[C:23]([Cl:3])=[O:24])=[C:19]([F:29])[CH:18]=2)=[N:8][CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 14207657HCID 14207657, compound

Product 1

HCID 14855598HCID 14855598, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (7.24 g, 0.0608 mole) was added to a stirred solution of 2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-2-fluorophenoxy)propanoic acid (21.0 g, 0.0553 mole), benzene (150 ml), and dimethyl formamide (0.3 g). Refluxing was effected for three hours. The benzene and residual thionyl chloride were removed by distillation under vacuum. The resulting amber colored oil (21 g) was shown to be the desired acid chloride by NMR and IR spectroscopy. This material was used directly in subsequent reactions.

Workup

  1. temperatureRefluxing
  2. customThe benzene and residual thionyl chloride were removed by distillation under vacuum

Sources & evidence

ORD record
ord-bfe5096a0c4741258a98ca2744a3d0ef
Source dataset
uspto-grants-1989_12
Patent number
US04888050

Reaction notes

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