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

HRID 658508Notes

Reaction equation

HRID 658508 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-04476d7e230b45209aca6cae7e8145c6
Source dataset
uspto-grants-2011_12
Patent number
US08076505B2

Reaction notes

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