2-Chloro-6-methylaniline → Benzenamine, 4-bromo-2-chloro-6-methyl-, hydrobromide (1:1)

HRID 2427493Notes

Reaction equation

HRID 2427493 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH2:9].[Br:10]Br>CO.C(O)(=O)C>[BrH:10].[Br:10][C:6]1[CH:5]=[C:4]([CH3:8])[C:3]([NH2:9])=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 2

HCID 68972-Chloro-6-methylanilineHCID 24408Bromine

Product 1

HCID 67252495Benzenamine, 4-bromo-2-chloro-6-methyl-, hydrobromide (1:1)

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent2×

Procedure

2-Chloro-6-methyl-phenylamine (5.00 g, 35.3 mmol) was dissolved in methanol (15 mL) and acetic acid was added (5 mL). The solution was chilled in an ice bath and a solution of bromine (1.8 mL) in acetic acid (15 mL) was added dropwise. After complete addition MeOH (5 mL) was added to dissolve the precipitated solid. The solvents were removed under reduced pressure and the residue was triturated with hexanes to provide the title compound as an off white solid (10.49 g, 99%). 1H NMR (300 MHz, MeOD): δ 7.42 (s, 1H), 7.28 (s, 1H), 2.42 (s, 3H).

Workup

  1. temperatureThe solution was chilled in an ice bath
  2. additionwas added
  3. dissolutionto dissolve the precipitated solid
  4. customThe solvents were removed under reduced pressure
  5. customthe residue was triturated with hexanes

Sources & evidence

ORD record
ord-c561d30f7ee94b499f5cc000ff935faa
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…