1,3-Dibromopropane → 1-[4-(3-Bromo-propoxy)-phenyl]-cyclohexanecarbonitrile

HRID 272920Notes

Reaction equation

HRID 272920 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:22][CH2:23][CH2:24][CH2:25]Br>CC(C)=O>[Br:22][CH2:23][CH2:24][CH2:25][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 198585061-(4-Hydroxyphenyl)cyclohexane-1-carbonitrile

Product 1

HCID 598375041-[4-(3-Bromo-propoxy)-phenyl]-cyclohexanecarbonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

1-(4-Hydroxyphenyl)cyclohexanecarbonitrile (2.0 g, 10 mmol) was taken in acetone (150 mL) and then Cs2CO3 (8.1 g, 25 mmol) was added followed by dropwise addition of 1,3 dibromopropane (5.1 mL, 50 mmol). The mixture was heated for 3 h at 70° C. After cooling and filtration, the mixture was concentrated and the residue was purified by flash chromatography (50 g silica gel, DCM) to provide the title compound (2.8 g, 87%). Note: presence of allyl derivative as impurity.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltration
  3. concentrationthe mixture was concentrated
  4. customthe residue was purified by flash chromatography (50 g silica gel, DCM)

Sources & evidence

ORD record
ord-5808d31f2c7c4558994a26b7e8007286
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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