Benzoyl Peroxide → 1-Bromo-3-(bromomethyl)-5-methylbenzene

HRID 378164

反応式

HRID 378164 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:28]N1C(=O)CCC1=O>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH3:9])[CH:3]=1)[CH2:8][Br:28]

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 136357Benzene, 1-bromo-3,5-dimethyl-

生成物 1

HCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzene収率 27.8%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To 5-bromo-m-xylene (24.03 g, 0.13 mole) in benzene (125 mL) was added benzoylperoxide (3.04 g, 0.013 mole). The reaction mixture was heated to reflux in a 250 mL round bottom flask. N-bromosuccinimide (18.15 g, 0.10 mole) was added in portions over 15 minutes. After 2 hours, heating was discontinued and the reaction mixture was allowed to cool to room temperature. Precipitated solids were removed by filtration and the filtrate was concentrated. The residue was taken up in hexane and additional solids were removed by filtration. The filtrate was passed through a small pad of silica gel and the filtrate was concentrated. The resultant yellow oil was titurated with MeOH over ice to give 3-bromo-5-methylbenzyl bromide (7.34 g) as a white solid. MS and NMR were consistent with the desired structure.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux in a 250 mL round bottom flask
  3. temperatureheating
  4. customPrecipitated solids
  5. customwere removed by filtration
  6. concentrationthe filtrate was concentrated
  7. customadditional solids were removed by filtration
  8. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-7be91d5fc2a145b7b63c46ddf403018b
出典データセット
uspto-grants-2000_02
特許番号
US06028223

関連ノート

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