Dichloromethane → 4-Bromo-2-(bromomethyl)-1-chlorobenzene

HRID 630039

반응식

HRID 630039 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH3:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.ClCCl>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][Br:10])[CH:3]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 6098995-Bromo-2-chlorotoluene

생성물 1

HCID 115582804-Bromo-2-(bromomethyl)-1-chlorobenzene수율 70%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 4-bromo-1-chloro-2-methylbenzene (5.0 g, 24.0 mmol), N-bromosuccinimide (4.4 g, 25.0 mmol), and benzoyl peroxide (700 mg, 2.9 mmol) in anhydrous carbon tetrachloride (85 mL) was stirred at reflux for 4 hours. Dichloromethane (50 mL) was added. The mixture was extracted with 1 N NaOH (1×150 mL) and brine (1×150 mL). The organic extract was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-5% EtOAc/hexanes), affording 4-bromo-2-(bromomethyl)-1-chlorobenzene (4.76 g, 70% yield). The product was used without further purification.

후처리

  1. temperatureat reflux for 4 hours
  2. extractionThe mixture was extracted with 1 N NaOH (1×150 mL) and brine (1×150 mL)
  3. extractionThe organic extract
  4. customwas recovered
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo
  9. customThe crude product was purified by flash chromatography (0-5% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-ed3849c3768241ef9ae0d89b7e3ab53d
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315521B2

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