Hydrochloric Acid → 3-Chloro-2,6-difluoroaniline

HRID 2367155Notes

Reaction equation

HRID 2367155 reaction equation
[Cl:1][C:2]1[C:3]([F:17])=[C:4]([NH:9]C(=O)OC(C)(C)C)[C:5]([F:8])=[CH:6][CH:7]=1.Cl>CO.O1CCOCC1>[Cl:1][C:2]1[C:3]([F:17])=[C:4]([C:5]([F:8])=[CH:6][CH:7]=1)[NH2:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86083514tert-Butyl (3-chloro-2,6-difluorophenyl)carbamate

Product 1

HCID 177507453-Chloro-2,6-difluoroanilineYield 92.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl (3-chloro-2,6-difluorophenyl)carbamate (437 mg, 1.66 mmol) in methanol (2 mL) was treated with 4 N hydrochloric acid in dioxane (2 mL) and heated for 1 min with a heat gun. After cooling, the volatile materials were removed in vacuo. The resulting residue was taken up in ethyl acetate and washed with sodium bicarbonate (sat). The organic phase was dried over magnesium sulfate, filtered, and concentrated yielding 3-chloro-2,6-difluoroaniline as a white solid (250 mg, 1.53 mmol, 92%). MS (EI) for C6H4ClF2N: 164 (MH+).

Workup

  1. temperatureheated for 1 min with a heat gun
  2. temperatureAfter cooling
  3. customthe volatile materials were removed in vacuo
  4. washwashed with sodium bicarbonate (sat)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b33453b416334c2781d1b024ac9a0681
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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