4-Bromophenol → 3-(4-Bromophenoxy)oxetane

HRID 1625026Notes

Reaction equation

HRID 1625026 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].CC1C=CC(S(O[CH:26]2[CH2:29][O:28][CH2:27]2)(=O)=O)=CC=1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:26]2[CH2:29][O:28][CH2:27]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 13153907Oxetan-3-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 573860513-(4-Bromophenoxy)oxetane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromophenol (2.5 g, 14.5 mmol) and K2CO3 (5.45 g, 39.4 mmol) were added to a solution of oxetan-3-yl 4-methylbenzenesulfonate (3.00 g, 13.1 mmol) in DMF (10 mL) in a sealed tube. The reaction was heated to 100° C. and stirred at this temperature for 24 h. The reaction was diluted with EtOAc and washed with water. The organic layer was dried (MgSO4), filtered and concentrated to afford the title compound. MS (GCMS) m/z 228. This material was used in subsequent steps without further purification.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9a0d3682140b49cbb655fa14c8623dfd
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

Loading…