Benzoyl Peroxide → 3',4'-Dichloro-2-fluoro-4-bromomethyl-biphenyl

HRID 658508노트

반응식

HRID 658508 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:6][C:7]=1[Cl:8].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.S([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][Br:17])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

7

반응물 4

HCID 7187Benzoyl PeroxideHCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 669167363',4'-Dichloro-2-fluoro-4-methyl-biphenyl

생성물 1

HCID 669167173',4'-Dichloro-2-fluoro-4-bromomethyl-biphenyl

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

3′,4′-dichloro-2-fluoro-4-methyl-biphenyl (29 g, 0.114 mol), N-bromosuccinimide (21.2 g, 0.119 mol), benzoyl peroxide (1.4 g, 0.004 mol) were dissolved in acetonitrile (190 ml). The mixture was refluxed for 3 hours, then cooled, mixed with a solution of sodium sulphite (2.2 g) in water (54 ml), stirred for 30 minutes and then allowed to rest to separate the phases. The lower aqueous phase was separated and extracted with dichloromethane (29 ml). The upper phase was concentrated under vacuum, mixed with water (10 ml), and dichloromethane (58 ml) and stirred. The organic phases were separated and put together, washed twice with water (29 ml), and concentrated under vacuum. The compound 3′,4′-dichloro-2-fluoro-4-bromomethyl-biphenyl was isolated as an orange oil (35.7 g, 94% yield).

후처리

  1. temperatureThe mixture was refluxed for 3 hours
  2. temperaturecooled
  3. customto separate the phases
  4. customThe lower aqueous phase was separated
  5. extractionextracted with dichloromethane (29 ml)
  6. concentrationThe upper phase was concentrated under vacuum
  7. additionmixed with water (10 ml), and dichloromethane (58 ml)
  8. stirringstirred
  9. customThe organic phases were separated
  10. washwashed twice with water (29 ml)
  11. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-04476d7e230b45209aca6cae7e8145c6
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076505B2

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