Potassium Carbonate → 3-Bromo-4-cyclobutoxybenzonitrile

HRID 254645Notes

Reaction equation

HRID 254645 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].Br[CH:12]1[CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:12]1[CH2:15][CH2:14][CH2:13]1)[C:5]#[N:6]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 753413-Bromo-4-hydroxybenzonitrileHCID 78110Bromocyclobutane

Product 1

HCID 668518283-Bromo-4-cyclobutoxybenzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

3-Bromo-4-hydroxybenzonitrile (2.0 g, 10.1 mmol), bromocyclobutane (2.7 g, 20.2 mmol), and K2CO3 (2.8 g, 20.2 mmol) were mixed in 5 mL of DMF and heated at 60° C. for 72 hours. The reaction was diluted with EtOAc washed with water, brine dried with MgSO4 and the solvent was removed. The product was purified by flash chromatography using a gradient from 0 to 30% EtOAc in hexane to provide the title compound. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.69-1.82 (m, 1H) 1.87-2.00 (m, 1H) 2.21-2.35 (m, 2H) 2.45-2.57 (m, 2H) 4.69-4.79 (m, 1H) 6.76 (d, J=8.48 Hz, 1H) 7.53 (dd, J=8.48, 2.03 Hz, 1H) 7.82 (d, J=2.03 Hz, 1H). MS (DCI/NH3) m/z 251.9 (M+H)+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried with MgSO4
  3. customthe solvent was removed
  4. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-3e13e49af4ac4de7b2228da9fb54beb9
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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