Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Chlorosuccinimide | HCID 31398 | — |
| Reactant | 4-bromo-2-tert-butylphenylamine | HCID 11959000 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67276324 | HCID 67276324 | 98.7% |
Reaction Steps
6.4 g (48 mmol) of N-chlorosuccinimide are added to a solution of 10 g (44 mmol) of 4-bromo-2-tert-butylphenylamine (example 1a) in 150 ml of DMF. The medium is heated at 70° C. for 2 hours. It is then poured into a saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic phases are combined and washed with water and then dried over sodium sulphate. The residue is chromatographed on silica gel (90/10 heptane/ethyl acetate). 11.4 g of 4-bromo-2-tert-butyl-6-chlorophenylamine are obtained in the form of an orange oil (yield=99%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163952B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-9d00c41e144640ff8c9e2c3a52dc7fcc |
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| Source note | uspto-grants-2012_04 |
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