2,4,6-Trifluorobenzoic acid → Tert-butyl 2,4,6-trifluorobenzoate

HRID 2048077Notes

Reaction equation

HRID 2048077 reaction equation
[C:1](=[O:12])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])OC(C)(C)C.[F:13][C:14]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[C:15]=1C(O)=O>CN(C)C1C=CN=CC=1.CC(O)(C)C>[F:13][C:14]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[C:15]=1[C:1]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:12]

Participants

5

Reactant 2

HCID 5203732,4,6-Trifluorobenzoic acidHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 58042440Tert-butyl 2,4,6-trifluorobenzoateYield 100.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
40 °C

Procedure

Di-tert-butyl carbonate (4.95 g, 22.7 mmol) was added to a solution of 2,4,6-trifluorobenzoic acid (2.0 g, 11.3 mmol) and 4-dimethylaminopyridine (139 mg, 1.14 mmol) in tBuOH (30 mL) and the reaction mixture was heated at 40° C. for 18 hours. The reaction mixture was then quenched with aqueous 1M HCl and extracted into EtOAc. The combined organics were washed with aqueous 1M NaOH, followed by brine, dried and concentrated in vacuo to afford the title compound as a pale yellow oil (2.63 g, 52% yield):

Workup

  1. customThe reaction mixture was then quenched with aqueous 1M HCl
  2. extractionextracted into EtOAc
  3. washThe combined organics were washed with aqueous 1M NaOH
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-541e1d96739c4a549945c49f7638f59c
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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