4-Bromostyrene → HCID 58288379, compound

HRID 1475633Notes

Reaction equation

HRID 1475633 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[FH:10].F.F.C(N(CC)CC)C.[Br:20]N1C(=O)CCC1=O>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([F:10])[CH2:7][Br:20])=[CH:4][CH:3]=1

Participants

5

Conditions

Temperature
0 °C

Procedure

5.0 g (27.31 mmol) of 4-bromostyrene were dissolved in 40 ml of dichloromethane, the mixture was cooled to 0° C. and 13.21 g (81.94 mmol) of triethylamine trihydrofluoride were added. 5.83 g (32.78 mmol) of N-bromosuccinimide were then added in three portions. The mixture was stirred at RT overnight. After dilution with dichloromethane, the reaction mixture was added to ice-water. The organic phase was washed successively with 1 N hydrochloric acid, water and saturated sodium bicarbonate solution, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase pentane). This gave 4.14 g (53.8% of theory) of the title compound.

Workup

  1. washThe organic phase was washed successively with 1 N hydrochloric acid, water and saturated sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (mobile phase pentane)

Sources & evidence

ORD record
ord-e5fca9cc6a434cff9bf2166feed5657d
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

Loading…