Ethyl Acetate → HCID 58994555, compound

HRID 1190217Notes

Reaction equation

HRID 1190217 reaction equation
[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH2:7][C:8]([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O.CCOC(C)=O>C(Cl)Cl>[Br:20][C:13]1[CH:12]=[C:11]([C:8]([CH3:10])([CH3:9])[CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:18])[CH3:19])[CH:16]=[CH:15][C:14]=1[NH2:17]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 58994419HCID 58994419, compound

Product 1

HCID 58994555HCID 58994555, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-phenylamine (as prepared in the previous step, 1.41 g, 5.04 mmol) in 25 mL of DCM at 0° C. was slowly added N-bromosuccinimide (NBS) (898 mg, 5.04 mmol) in three portions over five minutes. After stirring at RT for 2 h, the mixture was treated with 50 mL of EtOAc and washed with H2O (2×30 mL) and brine H2O (20 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (DCM) to give 1.59 g (88%) of the title compound as a light yellow oil. Mass spectrum (ESI, m/z): Calcd. for C16H28BrNOSi, 358.1 (M+H). found 358.4.

Workup

  1. customover five minutes
  2. washwashed with H2O (2×30 mL) and brine H2O (20 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (DCM)

Sources & evidence

ORD record
ord-52eb7bf13c504342bed8f37e9b5fa7ff
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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