Carbamic acid, N-(3-bromo-5-chloro-2-fluorophenyl)-, 1,1-dimethylethyl ester → 3-Bromo-5-chloro-2-fluorobenzenamine
Reaction equation
[Br:1][C:2]1[C:3]([F:17])=[C:4]([NH:9]C(=O)OC(C)(C)C)[CH:5]=[C:6]([Cl:8])[CH:7]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Br:1][C:2]1[C:3]([F:17])=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[NH2:9]Participants
3
Procedure
A solution of tert-butyl 3-bromo-5-chloro-2-fluorophenylcarbamate (900 mg, 2.78 mmol) in DCM/TFA (1:1, 20 mL) was stirred at rt for 1 h. The reaction mixture was concentrated, then the residue was taken up in ethyl acetate and washed with aqueous sodium bicarbonate and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to provide the crude title compound (736 mg). MS m/z 223.9 (M+1).
Workup
- concentrationThe reaction mixture was concentrated
- washwashed with aqueous sodium bicarbonate and brine
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d5c835e1a2044b3fb534ac2c093ccf64
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501758B2
Reaction notes
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