1,4-Dibromobutane → HCID 66822963, compound

HRID 331686Notes

Reaction equation

HRID 331686 reaction equation
[NH2:1][CH2:2][CH:3]([C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.Br[CH2:26][CH2:27][CH2:28][CH2:29]Br>C(#N)C>[CH2:4]([CH:3]([C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)[CH2:2][N:1]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 8471TriethylamineHCID 66746773HCID 66746773, compound

Product 1

HCID 66822963HCID 66822963, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 3-(1-amino-3-phenylpropan-2-yl)phenol (0.6 g, 2.6 mmol) dissolved in 40 ml acetonitrile was added triethylamine (0.81 ml, 5.8 mmol) followed by 1,4-dibromobutane (0.37 ml, 3.2 mmol). The mixture was heated to reflux for 3 h then poured on ice-water and extracted twice with dichloromethane. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and the solvent evaporated to obtain a yellow oil. m=665 mg (90%)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. additionthen poured on ice-water
  4. extractionextracted twice with dichloromethane
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customto obtain a yellow oil

Sources & evidence

ORD record
ord-e12da3edd7c143409e5cd252213fb53b
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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