Water → 4-(3-Bromopropyl)-1-chloro-2-methylbenzene

HRID 1093448Notes

Reaction equation

HRID 1093448 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]O)=[CH:4][C:3]=1[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32]N1C(=O)CCC1=O.O>C(Cl)Cl>[Br:32][CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:12])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 594075893-(4-Chloro-3-methyl-phenyl)-propan-1-ol

Product 1

HCID 665942494-(3-Bromopropyl)-1-chloro-2-methylbenzeneYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 67-2 (2.49 g) was dissolved in methylene chloride (45 ml), triphenylphosphine (3.90 g) and N-bromosuccinimide (2.64 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 2.5 hr. Water was added to the reaction mixture, and the mixture was extracted with methylene chloride and washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone) to give the object product (2.99 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2.5 hr
  3. extractionthe mixture was extracted with methylene chloride
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. additionDiethyl ether was added
  8. filtrationthe precipitated triphenylphosphine oxide was filtered off
  9. concentrationThe concentrate of the filtrate
  10. customwas purified by silica gel column chromatography (hexane alone)

Sources & evidence

ORD record
ord-a4c95e18c6134d77a2f5842120966185
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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