1,3-Dibromobenzene → 1-(3-Bromophenyl)-cyclobutanol

HRID 2303578Notes

Reaction equation

HRID 2303578 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.C([Li])CCC.[C:14]1(=[O:18])[CH2:17][CH2:16][CH2:15]1>O1CCCC1.CCCCCC>[Br:8][C:4]1[CH:3]=[C:2]([C:14]2([OH:18])[CH2:17][CH2:16][CH2:15]2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 79271,3-DibromobenzeneHCID 14496CyclobutanoneHCID 178418339Butyllithium

Product 1

HCID 184615711-(3-Bromophenyl)-cyclobutanolYield 66.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1,3-dibromo-benzene (2.36 grams, 10 mmol) in tetrahydrofuran at −78° C. was added a 1.6M solution of n-butyllithium (6.3 ml, 10 mmol) in hexane and stirred for 4 hours. Cyclobutanone (700 mg, 10 mmol) was then added in one portion. After stirring for 2 hours at −78° C., the reaction was quenched with 2N hydrochloric acid. The reaction was warmed to room temperature, diluted with water and extracted with ethyl acetate. The ethyl acetate layer was dried and evaporated to give 2.5 grams of crude product which was purified on silica gel eluting with 50% methylene chloride in hexane to give 1.5 grams of the titled compound.

Workup

  1. stirringAfter stirring for 2 hours at −78° C.
  2. customthe reaction was quenched with 2N hydrochloric acid
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried
  6. customevaporated
  7. customto give 2.5 grams of crude product which
  8. customwas purified on silica gel eluting with 50% methylene chloride in hexane

Sources & evidence

ORD record
ord-262eb6f471cd4b718da5b06097c52153
Source dataset
uspto-grants-2002_08
Patent number
US06433009B1

Reaction notes

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