N-bromobutanimide → HCID 58026177, compound

HRID 2387315Notes

Reaction equation

HRID 2387315 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:18])([CH3:17])[CH2:9][C@:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)=[C:4]([CH3:19])[CH:3]=1.C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:27][CH2:19][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[C:8]([CH3:17])([CH3:18])[CH2:9][C@:10]1([C:13]([F:16])([F:14])[F:15])[CH2:12][O:11]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 58026126HCID 58026126, compound

Product 1

HCID 58026177HCID 58026177, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 17.7 g (R)-2-[2-(4-fluoro-2-methylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (0.064 mol) in 250 mL of CCl4 was added 14.8 g (0.083 mol) of NBS followed by 1.5 g (0.006 mol) benzoyl peroxide and heated to 80° C. for 2 hours. The mixture was cooled to room temperature, diluted with 1800 mL of hexanes, filtered through a pad of CELITE® filter aid, and concentrated in vacuo. The crude mixture was chromatographed on silica gel using 0-5% ethyl acetate/hexanes to afford 24 g (69%) (R)-2-[2-(2-bromomethyl-4-fluorophenyl)-2-methylpropyl]-2-trifluoromethyloxirane.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of CELITE®
  3. filtrationfilter aid
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture was chromatographed on silica gel using 0-5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5992b3ae3d3c40b5bb389255a5c5155c
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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