Potassium Carbonate → HCID 58189116, compound

HRID 1423094Notes

Reaction equation

HRID 1423094 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH2:10][CH3:11])=[C:6]([OH:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:19]1[CH2:22][CH2:21][CH2:20]1>CN(C=O)C.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH2:10][CH3:11])=[C:6]([O:8][CH:19]2[CH2:22][CH2:21][CH2:20]2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 78110BromocyclobutaneHCID 66824870HCID 66824870, compound

Product 1

HCID 58189116HCID 58189116, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

The intermediate 5-bromo-2-ethoxy-phenol (15 g, 73.9 mmol) was dissolved in DMF (100 mL) then treated with anhydrous K2CO3 (20.4 g, 148 mmol) followed by the addition of bromocyclobutane (19.1 g, 128 mmol). The reaction was heated at 65° C. for 12 h, then cooled to room temperature, diluted with diethyl ether, and the solution washed with a 1 N aqeuous NaOH solution followed by water. The organic layer was then dried over MgSO4, filtered, and concentrated to afford titled compound as an oil (19.5 g, 90%). 1H NMR (CDCl3) 6.98 (dd, J=8.4, 2.1, 1H), 6.83 (d, J=2.4, 1H), 6.73 (d, J=8.7, 1H), 4.65-4.57 (m, 1H), 4.05 (q, J=7.1, 2H), 2.50-2.42 (m, 2H), 2.30-2.18 (m, 2H), 1.90-1.81 (m, 1H), 1.73-1.63 (m, 1H), 1.44 (t, J=7.1, 3H). 13C NMR 148.2, 147.8, 123.4 (CH), 117.0 (CH), 114.7 (CH), 112.7, 72.5 (CH), 64.8 (CH2), 30.6 (CH2), 14.7 (CH3), 13.1 (CH2). LC/MS (Method B) 4.18 min, [M+1]+ 271/273.

Workup

  1. temperaturecooled to room temperature
  2. washthe solution washed with a 1 N aqeuous NaOH solution
  3. dry with materialThe organic layer was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-39c99a07eeb64f23b6bed02a4b6dcac3
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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