Acetone → HCID 70873024, compound

HRID 1844691Notes

Reaction equation

HRID 1844691 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.[Li]CCCC.[CH3:18][C:19]([CH3:21])=[O:20]>C1COCC1.[NH4+].[Cl-]>[Br:12][C:4]1[CH:3]=[C:2]([C:19]([OH:20])([CH3:21])[CH3:18])[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 27611701,3-dibromo-5-tert-butylbenzeneHCID 178418339Butyllithium

Product 1

HCID 70873024HCID 70873024, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 1,3-dibromo-5-tert-butylbenzene (404 mg) in dry THF (10 mL) was added n-BuLi (0.84 mL) at −78° C. and after 20 min, acetone was added dropwise to the above solution at −78° C. and the mixture was stirred at this temperature for 30 min and at rt for 1 h, diluted with sat. NH4Cl and extracted with EA (3×30 mL). The organic layer was dried over Na2SO4, evaporated and purified by CC to give compound P23a (380 mg, 70%) as a white solid.

Workup

  1. extractionextracted with EA (3×30 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated
  4. custompurified by CC
  5. customto give compound P23a (380 mg, 70%) as a white solid

Sources & evidence

ORD record
ord-0fc5ce318b514858b5ba7fc2b4e7670d
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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