1,4-Dibromobutane → HCID 66822963, compound

HRID 591184Notes

Reaction equation

HRID 591184 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-cebacedb220542098715a57c96470999
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

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