N-bromobutanimide → 1-Cyclopropyl-1-(4-chlorophenyl)-4-bromo-4-(4-fluoro-3-phenoxyphenyl)butane

HRID 1588893Notes

Reaction equation

HRID 1588893 reaction equation
[CH:1]1([CH:4]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:9]=2)[CH2:3][CH2:2]1.[Br:29]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH:1]1([CH:4]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:5][CH2:6][CH:7]([Br:29])[C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 6451141Protrifenbute

Product 1

HCID 197548261-Cyclopropyl-1-(4-chlorophenyl)-4-bromo-4-(4-fluoro-3-phenoxyphenyl)butaneYield 88.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of 2.0 grams (0.005 mole of 1-cyclopropyl-1-(4-chlorophenyl)-4-(4-fluoro-3-phenoxyphenyl)butane and 0.9 gram (0.005 mole) of N-bromosuccinimide in 50 mL of carbon tetrachloride was irradiated for 2 hours with a sun lamp. The reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure, yielding 2.1 grams of 1-cyclopropyl-1-(4-chlorophenyl)-4-bromo-4-(4-fluoro-3-phenoxyphenyl)butane. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e85d715928924bee99af06b3e57d632c
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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