1,4-Dibromobenzene → 3-(4-Bromophenyl)oxetan-3-ol

HRID 385721Notes

Reaction equation

HRID 385721 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[O:14]1[CH2:17][C:16](=[O:18])[CH2:15]1.[NH4+].[Cl-]>C1COCC1.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]2([OH:18])[CH2:17][O:14][CH2:15]2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 78041,4-DibromobenzeneHCID 25517Ammonium ChlorideHCID 150242543-OxetanoneHCID 178418339Butyllithium

Product 1

HCID 583823793-(4-Bromophenyl)oxetan-3-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1,4-Dibromobenzene (2 g, 8.48 mmol) was taken up in THF (35 mL) and cooled to −78° C. before adding n-BuLi (3.39 mL, 8.48 mmol) dropwise. After stirring at −78° C. for 30 minutes, oxetan-3-one (0.611 g, 8.48 mmol) was added and the reaction was warmed to room temperature for 1 hour at which time water and saturated NH4Cl were added and the products were extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by flash silica gel column chromatography (6-50% EtOAc-hexanes) gave the title compound as a white solid.

Workup

  1. additionwere added
  2. extractionthe products were extracted into EtOAc (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash silica gel column chromatography (6-50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-3e7f2399325f49e2b1e91cf705dc0466
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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