1,3-Dibromopropane → 1-[4-(3-Bromopropoxy)-3-methoxyphenyl] phenylmethanone

HRID 1900380Notes

Reaction equation

HRID 1900380 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:14]=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH2:9]2)=[CH:4][C:3]=1[O:16][CH3:17].C([O-])([O-])=O.[K+].[K+].[Br:24][CH2:25][CH2:26][CH2:27]Br>C(#N)C>[Br:24][CH2:25][CH2:26][CH2:27][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:14]=[O:15])[CH:9]=[CH:10][CH:11]=[CH:12][CH2:13]2)=[CH:4][C:3]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 867482541-(4-Hydroxy-3-methoxyphenyl) phenylmethanone

Product 1

HCID 867482531-[4-(3-Bromopropoxy)-3-methoxyphenyl] phenylmethanoneYield 13.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(4-hydroxy-3-methoxyphenyl)phenyl-methanone (14 g, 61.4 mmol), K2CO3 (13 g, 92.1 mmol), and 1,3-dibromopropane (28 g, 86 mmol) in acetonitrile (400 ml) was heated at reflux for 4 hours. The reaction was followed by thin layer chromatography. At the end of the reaction, the inorganics were filtered off and the solvent was removed on a rotary evaporator. The residue was purified on a flash chromatographic column (SiO2, 140 g, eluted with 4:1 hexane:dichloromethane, 1.2 l) to give a partially solidified material: 15.44 g (72%). Recrystallization twice from ethanol gave 2.84 g of 1-[4-(3-bromopropoxy)-3-methoxyphenyl]phenylmethanone as white crystals, m.p.=88°-89° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customAt the end of the reaction
  4. filtrationthe inorganics were filtered off
  5. customthe solvent was removed on a rotary evaporator
  6. customThe residue was purified on a flash chromatographic column (SiO2, 140 g, eluted with 4:1 hexane:dichloromethane, 1.2 l)
  7. customto give a partially solidified material
  8. customRecrystallization twice from ethanol

Sources & evidence

ORD record
ord-2eebb9d3ae984ec4bc7ce93fb1e71f96
Source dataset
uspto-grants-1996_11
Patent number
US05574032

Reaction notes

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