2,3,4,6-tetrafluorobenzoic Acid → Tert-butyl 2,3,4,6-tetrafluorobenzoate

HRID 2048079Notes

Reaction equation

HRID 2048079 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[C:22]([F:23])=[C:21]([F:24])[CH:20]=[C:19]([F:25])[C:15]=1C(O)=O>CN(C)C1C=CN=CC=1.CC(O)(C)C>[F:13][C:14]1[C:22]([F:23])=[C:21]([F:24])[CH:20]=[C:19]([F:25])[C:15]=1[C:1]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:12]

Participants

5

Reactant 2

HCID 27765912,3,4,6-tetrafluorobenzoic AcidHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 58042506Tert-butyl 2,3,4,6-tetrafluorobenzoateYield 59%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
40 °C

Procedure

Di-tert-butyl carbonate (3.63 g, 16.7 mmol) was added to a mixture of 2,3,4,6-tetrafluorobenzoic acid (1.60 g, 8.88 mmol), 4-dimethylaminopyridine (102 mg, 0.83 mmol) in tBuOH (20 mL) and heated at 40° C. for 16 hours. The reaction mixture was quenched with aqueous 1M HCl and extracted with EtOAc. Combined organics were washed with aqueous 1M NaOH, then brine and evaporated in vacuo. The resulting crude was purified by silica gel chromatography eluting with 50% EtOAc in heptane to afford the title compound as a colourless oil (1.25 g, 59% yield):

Workup

  1. customThe reaction mixture was quenched with aqueous 1M HCl
  2. extractionextracted with EtOAc
  3. washCombined organics were washed with aqueous 1M NaOH
  4. custombrine and evaporated in vacuo
  5. customThe resulting crude was purified by silica gel chromatography
  6. washeluting with 50% EtOAc in heptane

Sources & evidence

ORD record
ord-eac1e9ec163c42cab4ae5cad56089821
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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