N-bromobutanimide → HCID 57809866, compound

HRID 2106047Notes

Reaction equation

HRID 2106047 reaction equation
[CH3:1][C:2]([C:12]1[C:20]2[O:19][CH2:18][O:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH2:3][C:4]1([C:7]([F:10])([F:9])[F:8])[CH2:6][O:5]1.[Br:21]N1C(=O)CCC1=O>C1COCC1.C(#N)C>[Br:21][C:14]1[CH:13]=[C:12]([C:2]([CH3:1])([CH3:11])[CH2:3][C:4]2([C:7]([F:8])([F:10])[F:9])[CH2:6][O:5]2)[C:20]2[O:19][CH2:18][O:17][C:16]=2[CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 57809836HCID 57809836, compound

Product 1

HCID 57809866HCID 57809866, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.1 g (0.35 mmol) of 4-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]benzo[1,3]dioxole in 5 mL of THF was added 0.06 g (0.35 mmol) of N-bromosuccinimide. The reaction was monitored by TLC. After stirring overnight, TLC showed starting material and a new slightly more polar spot. The reaction was concentrated in vacuo and the residue was diluted with hexanes. The resulting suspension was filtered to remove insoluble material and the filtrate was purified by chromatography over silica gel eluting with ethyl acetate-hexanes (0-10%) to afford an oil as a mixture of starting material and product (3.5:1) by proton NMR. The residue was dissolved in 3 mL of acetonitrile and 0.06 g (0.35 mmol) of N-bromosuccinimide was added. After 3 hours, a TLC indicated the reaction was complete and it was worked up as above to afford 0.07 g (54%) of 6-bromo-4-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]benzo[1,3]dioxole as a yellow oil.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionthe residue was diluted with hexanes
  3. filtrationThe resulting suspension was filtered
  4. customto remove insoluble material
  5. customthe filtrate was purified by chromatography over silica gel eluting with ethyl acetate-hexanes (0-10%)
  6. customto afford an oil
  7. additionas a mixture of starting material and product (3.5:1) by proton NMR
  8. waitAfter 3 hours

Sources & evidence

ORD record
ord-8a02fe9fa8b44b4591a8e2829d5671ff
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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