N-bromobutanimide → HCID 69265786, compound

HRID 899241Notes

Reaction equation

HRID 899241 reaction equation
[C:1]([Si:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([CH3:16])[CH:10]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:16][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[F:15])[O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 580060724-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-fluoro-2-methylbenzene

Product 1

HCID 69265786HCID 69265786, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl(4-fluoro-3-methylphenoxy)dimethylsilane (step 1, 30 g, 0.12 mol), N-bromosuccinimide (24 g, 0.13 mol) and benzoylperoxide (1.5 g, 6.2 mmol) in carbon tetrachloride (75 mL) was reflux under nitrogen atmosphere for 4 h. The reaction mixture was cooled at 0° C., and the white precipitate was filtered. The filtrate washed with sodium bicarbonate aqueous solution, dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography on silica gel eluting with hexane to afford 25 g (65%) of the title compound as a colorless oil:

Workup

  1. temperaturewas reflux under nitrogen atmosphere for 4 h
  2. filtrationthe white precipitate was filtered
  3. washThe filtrate washed with sodium bicarbonate aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with hexane

Sources & evidence

ORD record
ord-f0a7d5ac000542cfaef0751283cd313e
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

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