Trifluoroacetic anhydride → HCID 20468620, compound

HRID 1903348Notes

Reaction equation

HRID 1903348 reaction equation
F[C:2](F)(F)[C:3]([O:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])=O.[Cl:14][C:15]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][C:16]=1[O:17][C:18]1[CH:19]=[CH:20][C:21]([N+:30]([O-:32])=[O:31])=[C:22]([CH:29]=1)[C:23]([O:25]CCO)=[O:24]>CCOCC>[Cl:14][C:15]1[CH:36]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:34]=[CH:33][C:16]=1[O:17][C:18]1[CH:19]=[CH:20][C:21]([N+:30]([O-:32])=[O:31])=[C:22]([CH:29]=1)[C:23]([O:25][CH2:2][CH2:3][O:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])=[O:24]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 13259764HCID 13259764, compound

Product 1

HCID 20468620HCID 20468620, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Trifluoroacetic anhydride (8.4 g, 0.04 mole) was added portionwise to a solution of 2-hydroxyethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate (7 g, 0.017 mole) and 50 ml of ether. After holding at 30°-35° C. for an hour, the solution was allowed to stand at room temperature overnight. Excess trifluoroacetic anhydride was removed and 300 ml of ether was added. The ethereal solution was washed three times with water, dried over CaSO4 and concentrated to an oil. Kugelrohr distillation afforded 3.6 g of pure 2-(trifluoroacetoxy)ethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate as a gumming material (yield: 42.2%); nmr (CDCl3) δ 4.62 (s, 4H), 7.02-8.19 (m, 6H); ir (CHCl3) 1752, 1803 Cm-1.

Workup

  1. waitAfter holding at 30°-35° C. for an hour
  2. customExcess trifluoroacetic anhydride was removed
  3. addition300 ml of ether was added
  4. washThe ethereal solution was washed three times with water
  5. dry with materialdried over CaSO4
  6. concentrationconcentrated to an oil
  7. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-2b75958e8b43482f92947efd41d32030
Source dataset
uspto-grants-1984_03
Patent number
US04435588

Reaction notes

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