Nitrogen → 3'-Bromoacetophenone

HRID 42756

Reaction equation

HRID 42756 reaction equation
N#N.Br[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[CH:5]=1.[Li]CCCC.[NH4+].[Cl-].C1C[O:21][CH2:20][CH2:19]1>CCCCCC>[Br:10][C:6]1[CH:5]=[C:4]([C:20](=[O:21])[CH3:19])[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 947NitrogenHCID 79271,3-DibromobenzeneHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 165023'-Bromoacetophenone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 1,3-dibromobenzene (2.45 g, 10.07 mmol) in THF (25.0 mL) was treated at −78° C. with n-BuLi (4.0 mL of a 2.5M solution in hexane, 10.00 mmol). The reaction mixture was stirred for 30 min before N,N-dimethylacetaminde (1.50 mL, 16.13 mmol) was added and the solution was then allowed to warm to rt over 1 h. Sat. aq. NH4Cl was then added and the aq. layer was extracted with Et2O (3×50 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (20:1 hept-EA) gave the title compound as a white solid: TLC:rf (10:1 hept-EA)=0.28. LC-MS-conditions 02: tR=0.95 min.

Workup

  1. additionwas added
  2. extractionthe aq. layer was extracted with Et2O (3×50 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (20:1 hept-EA)

Sources & evidence

ORD record
ord-7f63863a680744e99c95ad88d6d31a6f
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Linked notes

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