Trifluoroacetic acid → 2-bromo-3-chloroaniline

HRID 2203205Notes

Reaction equation

HRID 2203205 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

HCID 6422Trifluoroacetic acidHCID 735533251463053-89-5

Product 1

HCID 118434422-bromo-3-chloroanilineYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. concentrationconcentrated
  2. additionWater (10 mL) was added to the residue
  3. extractionthe mixture was extracted with DCM (2×20 mL)
  4. customThe organic phase was separated
  5. washwashed with aqueous saturated NaHCO3 and saturated NaCl
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3997d2704b2a4a1593a1d0c7b638fe67
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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