Potassium Carbonate → 3-Bromo-4-cyclobutoxybenzonitrile

HRID 340645Notes

Reaction equation

HRID 340645 reaction equation
Br[CH:2]1[CH2:5][CH2:4][CH2:3]1.[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[OH:15])[C:10]#[N:11].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][CH:2]1[CH2:5][CH2:4][CH2:3]1)[C:10]#[N:11]

Participants

6

Reactant 3

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

Product 1

HCID 668518283-Bromo-4-cyclobutoxybenzonitrileYield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromocyclobutane (2.7 g, 20.2 mmol), 3-bromo-4-hydroxybenzonitrile (2.0 g, 10.1 mmol), and K2CO3 (2.8 g, 20.2 mmol) were mixed in 5 mL of dimethylformamide and reacted at 60° C. for 72 hours. The mixture was diluted with ethyl acetate, washed with water, brine, dried with MgSO4, filtered, and the solvent removed under reduced pressure. The residue was chromatographed (SiO2) using a gradient from hexane to 30% ethyl acetate in hexane over 500 mL to afford the title compound. (2.2 g, 8.7 mmol, 86% yield). 1H NMR (300 MHz, CDCl3) 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. customreacted at 60° C. for 72 hours
  2. washwashed with water, brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was chromatographed (SiO2)

Sources & evidence

ORD record
ord-ffac9034218349499b09675a3ff4cdb6
Source dataset
uspto-grants-2014_11
Patent number
US08895592B2

Reaction notes

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