3-Iodoaniline → 4-Bromo-3-iodoaniline
Reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Br:9]C1C(=O)C(Br)=CC(Br)(Br)C=1.[OH-].[Na+]>C(Cl)Cl>[Br:9][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[CH:3][C:2]=1[I:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To a solution of 3-iodoaniline (12 mL, 100 mmol) in 400 mL CH2Cl2 at −10° C. was added in portions 2,4,4,6-tetrabromo-2,5-cyclohexadienone (45.1 g, 110 mmol) while maintaining an internal temperature of −10° C. After stirring for 4 hours, 150 mL of 1N NaOH was added, and the product was extracted with CH2Cl2. The combined extracts were washed with water and then brine and dried over Na2SO4. After concentration in vacuo the crude product was recrystallized with 2:1 hexanes:toluene to yield the desired product.
Workup
- extractionthe product was extracted with CH2Cl2
- washThe combined extracts were washed with water
- dry with materialbrine and dried over Na2SO4
- concentrationAfter concentration in vacuo the crude product
- customwas recrystallized with 2:1 hexanes
Sources & evidence
- ORD record
- ord-d1a5f65a0fa542e1a847c8dd584d7b33
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168815B2
Reaction notes
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