Water → 1-Amino-2-bromo-6-tert-butoxy-4-nitronaphthalene

HRID 2306236Notes

Reaction equation

HRID 2306236 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:10]=2)[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O.O.C(Cl)Cl>C(O)(=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[CH:9][CH:10]=2)[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][C:3]=1[Br:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 184335291-Amino-6-tert-butoxy4-nitronaphthalene

Product 1

HCID 184335781-Amino-2-bromo-6-tert-butoxy-4-nitronaphthalene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 1-amino-6-tert-butoxy-4-nitronaphthalene, as described above in Step E, (2.02 g, 7.76 mmol) in acetic acid (55 mL) was added N-bromosuccinimide (1.45 g, 8.15 mmol), portionwise. The reaction mixture was stirred at ambient temperature for 1 hour, then H2O (150 mL) and CH2Cl2 (300 mL) were added and the organic layer was extracted. The organic extract was washed with saturated aqueous Na2CO3 (2×100 mL), then brine (100 mL), then dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated with hexane-Et2O to provide the titled product.

Workup

  1. extractionthe organic layer was extracted
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous Na2CO3 (2×100 mL)
  4. dry with materialbrine (100 mL), then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with hexane-Et2O

Sources & evidence

ORD record
ord-5b795d04ef1849059d057cc1e0672e07
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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