Trifluoroacetic acid → 2-Bromo-3-chloroaniline
Reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[Br:15])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:15][C:9]1[C:10]([Cl:14])=[CH:11][CH:12]=[CH:13][C:8]=1[NH2:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To tert-butyl(2-bromo-3-chlorophenyl)carbamate (0.4 g) in DCM (20 mL) was added TFA (10 mL). The reaction mixture was stirred at RT for 3 hours and then concentrated. Water (10 mL) was added to the residue, and the mixture was extracted with DCM (2×20 mL). The organic phase was separated, washed with aqueous saturated NaHCO3 and saturated NaCl, dried over anhydrous Na2SO4, and concentrated to give the title compound as a solid (0.2 g, 77%). 1H NMR (400 MHz, CDCl3) δ 7.03-6.99 (1H, m), 6.85-6.83 (1H, d, J=8.0 Hz), 6.65-6.63 (1H, d, J=8.0 Hz), 4.25 (2H, s).
Workup
- concentrationconcentrated
- additionWater (10 mL) was added to the residue
- extractionthe mixture was extracted with DCM (2×20 mL)
- customThe organic phase was separated
- washwashed with aqueous saturated NaHCO3 and saturated NaCl
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3997d2704b2a4a1593a1d0c7b638fe67
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365566B2
Reaction notes
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