1-Bromo-4-fluorobenzene → 3-((4-Bromophenoxy)methyl)oxetane

HRID 338438Notes

Reaction equation

HRID 338438 reaction equation
[O:1]1[CH2:4][CH:3]([CH2:5][OH:6])[CH2:2]1.[H-].[Na+].[Br:9][C:10]1[CH:15]=[CH:14][C:13](F)=[CH:12][CH:11]=1>CN(C=O)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([O:6][CH2:5][CH:3]2[CH2:4][O:1][CH2:2]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 99931-Bromo-4-fluorobenzeneHCID 24758Sodium hydrideHCID 11521066Oxetan-3-ylmethanol

Product 1

HCID 601694283-((4-Bromophenoxy)methyl)oxetaneYield 15.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of oxetan-3-ylmethanol (1.00 g, 11.3 mmol) in DMF (10 mL) was added NaH (300 mg, 13.6 mmol) at 0° C. The mixture was then stirred at 0° C. for 10 min. 1-Bromo-4-fluorobenzene (2.30 g, 13.6 mmol) was added to the solution. The mixture was stirred at 90° C. for 2 h. The mixture was partitioned between water and EtOAc (30 mL×3). The combined organics was dried and concentrated to give the title compound (420 mg, 15% yield) as a yellow oil.

Workup

  1. stirringThe mixture was stirred at 90° C. for 2 h
  2. customThe mixture was partitioned between water and EtOAc (30 mL×3)
  3. customThe combined organics was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-69e6a41085fa4b72ad4a85dc696e6760
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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