Benzoyl Peroxide → 1-(Bromomethyl)-3-[(2,2-dichloroethenyl)oxy]benzene
Reaction equation
[Cl:1][C:2]([Cl:12])=[CH:3][O:4][C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]([Cl:12])=[CH:3][O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[CH2:11][Br:13]Participants
Procedure
3-Tolyl 2,2-dichlorovinyl ether (12.2 g) was dissolved in carbon tetrachloride (75 ml), and N-bromosuccinimide (12.0 g) and a trace of wet benzoyl peroxide added, and the mixture refluxed for 3 hours. After filtration the solvent was evaporated from the filtrate, and the residue dissolved in ether and extracted with 1% w/v sodium hydroxide solution. The ethereal solution was dried over anhydrous magnesium sulphate, the solvent removed by evaporation under reduced pressure, and the residual oil distilled to yield a fraction boiling at 150° C/0.5 mm Hg. This fraction was shown by NMR to contain about 65% of the required product together with about 30% of unchanged starting material, the remainder being a small proportion of the dibromomethyl compound.
Workup
- temperaturethe mixture refluxed for 3 hours
- filtrationAfter filtration the solvent
- customwas evaporated from the filtrate
- dissolutionthe residue dissolved in ether
- extractionextracted with 1% w/v sodium hydroxide solution
- dry with materialThe ethereal solution was dried over anhydrous magnesium sulphate
- customthe solvent removed by evaporation under reduced pressure
- distillationthe residual oil distilled
- customto yield a fraction boiling at 150° C/0.5 mm Hg
Sources & evidence
- ORD record
- ord-5f86136d51444f23bd66c3d7fe5279f9
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04091110
Reaction notes
Loading…