Trimethylsilyl triflate → 1-[4-(Benzyloxy)-3-methylphenyl]-2-bromoethanone

HRID 920528

Reaction equation

HRID 920528 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C1C(=O)N([Br:47])C(=O)C1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH2:16][Br:47])=[CH:11][C:10]=1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 67184N-bromobutanimideHCID 81531DiisopropylethylamineHCID 12969325Ethanone, 1-[3-methyl-4-(phenylmethoxy)phenyl]-

Product 1

HCID 129693271-[4-(Benzyloxy)-3-methylphenyl]-2-bromoethanoneYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-benzyloxy-3-methyl-phenyl)-ethanone (12.89 g; 53.1 mmol) in CH2Cl2 was added, dropwise, at 0° C., DIPEA (10.9 mL; 63.7 mmol) and trimethylsilyl trifluoromethanesulfonate (11.1 mL; 61.1 mmol). The resulting mixture was stirred at 0° C. for 1 hour, and subsequently, NBS (10.87 g; 61.1 mmol) was added in one portion. The mixture was allowed to warm to RT stirred overnight. Then the mixture was concentrated in vacuo, the residue dissolved in EtOAc, washed with water twice, and brine, dried (MgSO4), filtered, and concentrated in vacuo to afford 1-(4-benzyloxy-3-methyl-phenyl)-2-bromo-ethanone (11.90 g).

Workup

  1. customat 0° C.
  2. temperatureto warm to RT
  3. stirringstirred overnight
  4. concentrationThen the mixture was concentrated in vacuo
  5. dissolutionthe residue dissolved in EtOAc
  6. washwashed with water twice
  7. dry with materialbrine, dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe1b9589b55747c4ba87726a178f5938
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Linked notes

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