Carbon tetrabromide → 1-(3,5-Dimethylphenoxy)-2-bromopropane

HRID 1975538Notes

Reaction equation

HRID 1975538 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:21].[CH3:25][CH:26](O)[CH2:27][O:28][C:29]1[CH:34]=[C:33]([CH3:35])[CH:32]=[C:31]([CH3:36])[CH:30]=1>C(Cl)Cl>[CH3:36][C:31]1[CH:30]=[C:29]([CH:34]=[C:33]([CH3:35])[CH:32]=1)[O:28][CH2:27][CH:26]([Br:21])[CH3:25]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 110739942-Propanol, 1-(3,5-dimethylphenoxy)-

Product 1

HCID 191002941-(3,5-Dimethylphenoxy)-2-bromopropaneYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.94 Gram (3.6 mmol) of triphenylphosphine and 1.49 g (4.5 mmol) of carbon tetrabromide were added to a solution prepared by dissolving 0.54 g (3 mmol) of 1-methyl-2-(3,5-dimethylphenoxy)ethanol in 10 ml of methylene chloride, and the resultant mixture was stirred at room temperature for 30 minutes. After the reaction, the solid was separated by filtration, and the remaining methylene chloride solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1 (v/v)) to give 0.54 g of 1-(3,5-dimethylphenoxy)-2-bromopropane (yield 74.7%).

Workup

  1. customprepared
  2. customAfter the reaction
  3. customthe solid was separated by filtration
  4. concentrationthe remaining methylene chloride solution was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1 (v/v))

Sources & evidence

ORD record
ord-619da100a3a84020af9a517059a1b0fc
Source dataset
uspto-grants-1994_02
Patent number
US05286905

Reaction notes

Loading…