1,3-dibromo-5-tert-butylbenzene → HCID 86719128, compound

HRID 1844695Notes

Reaction equation

HRID 1844695 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([Br:12])[CH:3]=1.[O:13]1[CH2:16][C:15](=[O:17])[CH2:14]1>C1COCC1.[Li]CCCC.[NH4+].[Cl-]>[Br:12][C:4]1[CH:3]=[C:2]([C:15]2([OH:17])[CH2:16][O:13][CH2:14]2)[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=1

Participants

6

Reactant 2

HCID 27611701,3-dibromo-5-tert-butylbenzeneHCID 150242543-Oxetanone

Product 1

HCID 86719128HCID 86719128, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolventHCID 178418339ButyllithiumSolvent

Procedure

To a solution of 1,3-dibromo-5-(tert-butyl)benzene (316 mg, 1.05 mmol) in dry THF (15 mL), n-BuLi (1 mL, 2.5M) was added dropwise under N2 at −78° C. The mixture was stirred at this temperature for 1 h. Then oxetan-3-one (91 mg, 1.27 mmol) was added and the mixture was stirred at rt overnight, diluted with aq. NH4Cl (20 mL) and extracted with EA. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the product P29a (120 mg, 40%) as a yellow solid.

Workup

  1. stirringthe mixture was stirred at rt overnight
  2. extractionextracted with EA
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give the product P29a (120 mg, 40%) as a yellow solid

Sources & evidence

ORD record
ord-30a4fd1bac9148929928d03cc7125e25
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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