Benzoyl Peroxide → HCID 117690398, compound

HRID 508117Notes

Reaction equation

HRID 508117 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])[CH3:10].[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>CCOC(C)=O>[Br:19][CH2:10][C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])=[CH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 117690248HCID 117690248, compound

Product 1

HCID 117690398HCID 117690398, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A stirred solution of 1-[1-(2-chlorophenyl)prop-1-en-2-yl]-2,4-difluorobenzene (680 mg, 2.56 mmol), N-bromosuccinimide (823 mg, 4.62 mmol) and benzoyl peroxide (30 mg) in AcOEt (15 ml) was heated under reflux for 3 h. After cooling to room temperature, the reaction mixture was diluted with AcOEt and washed with water, and the combined organic phases were dried and concentrated to dryness under reduced pressure. Purification by chromatography on silica gel gave 1-[3-bromo-1-(2-chlorophenyl)prop-1-en-2-yl]-2,4-difluorobenzene as a 52/48 mixture of diastereoisomers [colourless oil, 792 mg, yield 85%; GC/MS: m/z=344 (M+); HPLC/MS: log P(HCOOH)=4.80 (major diastereoisomer), 5.25 (minor diastereoisomer)].

Workup

  1. temperatureunder reflux for 3 h
  2. washwashed with water
  3. customthe combined organic phases were dried
  4. concentrationconcentrated to dryness under reduced pressure
  5. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-58626a37a0714ac98fdb54e9d9308a75
Source dataset
uspto-grants-2015_08
Patent number
US09095136B2

Reaction notes

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