Hydrochloric Acid → 3-Chloro-2,6-difluoroaniline
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
Product 1
Reagents, catalysts & solvents 2
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
- temperatureheated for 1 min with a heat gun
- temperatureAfter cooling
- customthe volatile materials were removed in vacuo
- washwashed with sodium bicarbonate (sat)
- dry with materialThe organic phase was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b33453b416334c2781d1b024ac9a0681
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697737B2
Reaction notes
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