2-Bromoaniline → HCID 21914268, compound

HRID 2421398Notes

Reaction equation

HRID 2421398 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Br[CH2:10][CH:11]([OH:15])[CH2:12][CH2:13]Br.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[N:4]1[CH2:13][CH2:12][CH:11]([OH:15])[CH2:10]1

Participants

6

Reactant 3

HCID 119922-BromoanilineHCID 295701,4-Dibromo-2-butanolHCID 81531Diisopropylethylamine

Product 1

HCID 21914268HCID 21914268, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-Bromoaniline (2 g) was heated with 1,4-dibromo-2-butanol (1.58 ml) and diisopropylethylamine (4.9 ml) in toluene (10 ml) at reflux for 20 h. The reaction mixture was allowed to cool, diluted with water (60 ml) and the aqueous phase extracted with ethyl acetate (3×30 ml). The combined extracts were washed with water, brine, dried (MgSO4), filtered and evaporated. The residue was adsorbed onto silica and purified by column chromatography, eluting with a gradient of 0-20% ethyl acetate in isohexane, to afford the product as a yellow oil (2.30 g).

Workup

  1. temperatureat reflux for 20 h
  2. temperatureto cool
  3. extractionthe aqueous phase extracted with ethyl acetate (3×30 ml)
  4. washThe combined extracts were washed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by column chromatography
  9. washeluting with a gradient of 0-20% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-fb2e16e18c9949e38f720219930769bc
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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